Substituted furano-/thienocycloalkylamino-2-pyrimidine derivatives and use thereof for controlling undesired plant growth

ABSTRACT

What are described are compounds of the general formula (I) and agrochemically acceptable salts thereof 
                         
their use in crop protection and processes for their preparation.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a National Stage entry of International ApplicationNo. PCT/EP2016/067035, filed Jul. 18, 2016, which claims priority toEuropean Patent Application No. 15178186.1, filed Jul. 24, 2015.

BACKGROUND Field

The invention relates to the technical field of crop protectioncompositions, particularly to that of herbicides for selective controlof broad-leaved weeds and weed grasses in crops of useful plants and inthe ornamental garden sector and for general control of broad-leavedweeds and weed grasses in areas of the environment where plant growth isdisruptive.

More particularly, the invention relates to substitutedfurano-/thienocycloalkylamino-2-pyrimidine derivatives, to processes forpreparation thereof and to the use thereof for control of harmfulplants.

Description of Related Art

The compounds of the formula (I) according to the invention have, in the2 position of the pyrimidine, a partially hydrogenated bicyclicsubstituent attached via an amine to the aromatic system in the alphaposition, where the pyrimidine may also be substituted in the 4position, 5 position and 6 position and adjacent substituents may form aring.

The herbicidal action of diaminopyrimidines and also ofmonoaminopyrimidines is already known from the prior art.

Monoaminopyrimidine derivatives having herbicidal action, namely5-aminopyrimidine derivatives, are disclosed, for example, in WO2013/144187 A1, while 2,4-diaminopyrimidines and the use thereof in thecrop protection sector have been described, for example, in EP 0523533A1, WO 2010/076009 and WO 2010/076010. 2,4-Diaminopyrimidines with abicyclic radical which have (1R,2S) configuration on the bridged andadjacent carbon atoms and additionally feature herbicidal efficacy areknown from US 2010/0167934 A1.

Also known are herbicidally active substitutedthienocycloalk(en)ylamino-1,3,5-triazines, and these are described, forexample, in the publications WO 2003/070710 A1, JP 2002020383 (includingfurans) and DE 19921883.

However, the use of the known pyrimidine and triazine derivatives asselective herbicides for the control of harmful plants or as plantgrowth regulators in various crops of useful plants frequently entailsan application rate that incurs high costs or results in unwanted damageto the useful plants. Moreover, in many cases, the use of the activecompounds is uneconomic owing to comparatively high production costs.

It is therefore desirable to provide alternative chemical activeingredients based on furano-/thienocycloalkylamino-2-pyrimidinederivatives which can be used as herbicides or plant growth regulatorsand which are associated with certain advantages compared to systemsknown from the prior art.

SUMMARY

Accordingly, it is an object of the present invention to providealternative furano-/thienocycloalkylamino-2-pyrimidine derivatives whichcan be used as herbicides or plant growth regulators, havingsatisfactory herbicidal action and a broad spectrum of activity againstharmful plants and/or having high selectivity in crops of useful plants.

Moreover, compared to the pyrimidine derivatives known from the priorart, the alternative furano-/thienocycloalkylamino-2-pyrimidinederivatives are to display a better profile of properties, particularlybetter herbicidal activity against harmful plants, a broader spectrum ofharmful plants and/or higher selectivity in crops of useful plants.

The object is achieved by means of specifically substitutedfurano-/thienocycloalkylamino-2-pyrimidine derivatives of the formula(I) or an agrochemically acceptable salt thereof, which canadvantageously be used as herbicides and also as plant growthregulators.

The present invention therefore provides compounds of the generalformula (I)

and the agrochemically acceptable salts thereof, where

-   A¹, A² and A³ each independently of one another are selected from    the group consisting of O, S, CR⁹, CR¹⁰ and CR¹¹, where exactly one    atom of A¹, A² and A³ is O or S;-   R⁹, R¹⁰ and R¹¹ each independently of one another are selected from    the group consisting of hydrogen, halogen, cyano, C(O)OH, C(O)NH₂,    (C₁-C₆)-alkyl, (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkyloxycarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-dialkylaminocarbonyl,    (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,    (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-alkynylcarbonyl, (C₂-C₆)-haloalkynylcarbonyl,    (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyloxy,    (C₂-C₆)-alkynyloxycarbonyl, (C₂-C₆)-haloalkynyloxycarbonyl and    nitro;-   R¹ and R² each independently of one another are selected from the    group consisting of    -   halogen, hydroxy, nitro, amino, cyano, C(O)NH₂;    -   (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl,        (C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,        (C₁-C₆)-haloalkylcarbonyloxy,        (C₁-C₆)-alkylcarbonyl-(C₁-C₄)-alkyl;    -   (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkoxycarbonyl,        (C₁-C₆)-haloalkoxycarbonyl,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-halogenalkyl;    -   (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkenylcarbonyl,        (C₂-C₆)-haloalkenylcarbonyl, (C₂-C₆)-alkenyloxy,        (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-alkenyloxycarbonyl,        (C₂-C₆)-haloalkenyloxycarbonyl;    -   (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-alkynylcarbonyl,        (C₂-C₆)-haloalkynylcarbonyl, (C₂-C₆)-alkynyloxy,        (C₂-C₆)-haloalkynyloxy, (C₂-C₆)-alkynyloxycarbonyl,        (C₂-C₆)-haloalkynyloxycarbonyl;    -   tri-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,        di-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,        mono-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl;        phenylsilyl-(C₂-C₆)-alkynyl;    -   (C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy, (C₆-C₁₄)-arylcarbonyl and        (C₆-C₁₄)-aryloxycarbonyl which may each be substituted at the        aryl moiety by halogen, (C₁-C₆)-alkyl and/or (C₁-C₆)-haloalkyl;    -   (C₆-C₁₄)-aryl-(C₁-C₆)-alkyl, (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxy,        (C₆-C₁₄)-aryl-(C₁-C₆)-alkyl-carbonyl,        (C₆-C₁₄)-aryl-(C₁-C₆)-alkyl-carbonyloxy,        (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyl,        (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyloxy;    -   aminocarbonyl-(C₁-C₆)-alkyl,        di-(C₁-C₆)-alkylaminocarbonyl-(C₁-C₆)-alkyl;    -   N—((C₁-C₆)-haloalkanoyl)-amino-carbonyl,        mono-((C₆-C₁₄)-aryl)-amino-carbonyl,        di-((C₆-C₁₄)-aryl)-amino-carbonyl;    -   (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy;    -   (C₃-C₈)-cycloalkyl, which may optionally be substituted at the        cycloalkyl radical by (C₁-C₆)-alkyl and/or halogen;        (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxy,        (C₃-C₈)-cycloalkylcarbonyl, (C₃-C₈)-cycloalkoxycarbonyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyl,        (C₃-C₈)-cycloalkylcarbonyloxy, (C₃-C₈)-cycloalkoxycarbonyloxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyloxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyloxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyloxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyloxy;    -   (C₃-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkenyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxy,        (C₃-C₈)-cycloalkenylcarbonyl, (C₃-C₈)-cycloalkenyloxycarbonyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyl,        (C₃-C₈)-cycloalkenylcarbonyloxy,        (C₃-C₈)-cycloalkenyloxycarbonyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyloxy;    -   hydroxy-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkoxy,        cyano-(C₁-C₆)-alkoxy, cyano-(C₁-C₆)-alkyl; and    -   (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,        (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-haloalkylthio,        (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,        (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,        (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-alkylthio-(C₁-C₆)-haloalkyl,        (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkylthio-(C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-alkylsulfonyloxy, (C₁-C₆)-haloalkylsulfonyloxy,        (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylthiocarbonyl,        (C₁-C₆)-alkylthiocarbonyloxy, (C₁-C₆)-haloalkylthiocarbonyloxy,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyl,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyloxy;        (C₄-C₁₄)-arylsulfonyl, (C₆-C₁₄)-arylthio, (C₆-C₁₄)-arylsulfinyl,        (C₃-C₈)-cycloalkylthio, (C₃-C₈)-alkenylthio,        (C₃-C₈)-cycloalkenylthio and (C₃-C₆)-alkynylthio;-   R³ is selected from the group consisting of    -   hydrogen, halogen, hydroxy, nitro, amino, cyano, C(O)OH,        C(O)NH₂;    -   (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl,        (C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,        (C₁-C₆)-haloalkylcarbonyloxy,        (C₁-C₆)-alkylcarbonyl-(C₁-C₄)-alkyl;    -   (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkoxycarbonyl,        (C₁-C₆)-haloalkoxycarbonyl,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-halogenalkyl;    -   (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkenylcarbonyl,        (C₂-C₆)-haloalkenylcarbonyl, (C₂-C₆)-alkenyloxy,        (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-alkenyloxycarbonyl,        (C₂-C₆)-haloalkenyloxycarbonyl;    -   (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-alkynylcarbonyl,        (C₂-C₆)-haloalkynylcarbonyl, (C₂-C₆)-alkynyloxy,        (C₂-C₆)-haloalkynyloxy, (C₂-C₆)-alkynyloxycarbonyl,        (C₂-C₆)-haloalkynyloxycarbonyl;    -   tri-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,        di-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,        mono-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl;        phenylsilyl-(C₂-C₆)-alkynyl; (C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy,        (C₆-C₁₄)-arylcarbonyl and (C₆-C₁₄)-aryloxycarbonyl which may        each be substituted at the aryl moiety by halogen, (C₁-C₆)-alkyl        and/or (C₁-C₆)-haloalkyl;    -   (C₆-C₁₄)-aryl-(C₁-C₆)-alkyl, (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxy,        (C₆-C₁₄)-aryl-(C₁-C₆)-alkyl-carbonyl,        (C₆-C₁₄)-aryl-(C₁-C₆)-alkyl-carbonyloxy,        (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyl,        (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyloxy;    -   aminocarbonyl-(C₁-C₆)-alkyl,        di-(C₁-C₆)-alkylaminocarbonyl-(C₁-C₆)-alkyl;    -   N—((C₁-C₆)-haloalkanoyl)-amino-carbonyl,        mono-((C₆-C₁₄)-aryl)-amino-carbonyl,        di-((C₆-C₁₄)-aryl)-amino-carbonyl;    -   (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy;    -   (C₃-C₈)-cycloalkyl, which may optionally be substituted at the        cycloalkyl radical by (C₁-C₆)-alkyl and/or halogen;        (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxy,        (C₃-C₈)-cycloalkylcarbonyl, (C₃-C₈)-cycloalkoxycarbonyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyl,        (C₃-C₈)-cycloalkylcarbonyloxy, (C₃-C₈)-cycloalkoxycarbonyloxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyloxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyloxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyloxy,    -   (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyloxy;        (C₃-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkenyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxy,        (C₃-C₈)-cycloalkenylcarbonyl, (C₃-C₈)-cycloalkenyloxycarbonyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyl,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyl,        (C₃-C₈)-cycloalkenylcarbonyloxy,        (C₃-C₈)-cycloalkenyloxycarbonyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyloxy,        (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyloxy;    -   hydroxy-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkoxy,        cyano-(C₁-C₆)-alkoxy, cyano-(C₁-C₆)-alkyl; and    -   (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,        (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-haloalkylthio,        (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,        (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,        (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-alkylthio-(C₁-C₆)-haloalkyl,        (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkylthio-(C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-alkylsulfonyloxy, (C₁-C₆)-haloalkylsulfonyloxy,        (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylthiocarbonyl,        (C₁-C₆)-alkylthiocarbonyloxy, (C₁-C₆)-haloalkylthiocarbonyloxy,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyl,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyloxy;        (C₄-C₁₄)-arylsulfonyl, (C₆-C₁₄)-arylthio, (C₆-C₁₄)-arylsulfinyl,        (C₃-C₈)-cycloalkylthio, (C₃-C₈)-alkenylthio,        (C₃-C₈)-cycloalkenylthio, (C₃-C₆)-alkynylthio; or-   R¹ may be attached to R² via a bond, resulting in a 5- to 7-membered    partially hydrogenated carbocycle or heterocycle having at least one    heteroatom selected from the group consisting of N, O, S and P,    which carbocycle or heterocycle is optionally substituted by one or    more substituents selected from the group consisting of hydroxy, ═O,    ═N—O—H, ═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl    substituted by one or more identical or different halogen atoms,    (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl and (C₁-C₆)-haloalkyl, and-   R³ is as defined above, but preferably represents hydrogen or amino;-   R⁴ is selected from the group consisting of hydrogen, (C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxycarbonyl    and aminocarbonyl;-   R⁵ and R⁶ are each independently of one another selected from the    group consisting of hydrogen, hydroxy, (C₁-C₆)-alkyl,    (C₁-C₆)-alkylphenyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy and    (C₁-C₆)-haloalkoxy; or the radicals R⁵ and R⁶ together with the    carbon atom to which they are attached form a 3- to 7-membered ring;-   R⁷ and R⁸ are each independently of one another selected from the    group consisting of hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy,    (C₆-C₁₄)-arylcarbonyl and (C₆-C₁₄)-aryloxycarbonyl; or the radicals    R⁷ and R⁸ together form a (C₁-C₇)-alkylene group which may contain    one or more oxygen and/or sulfur atoms, where the (C₁-C₇)-alkylene    group may be mono- or polysubstituted by halogen and the respective    halogen substituents may be identical or different;-   X represents a bond (if n=1 or 2) or is selected from the group    consisting of O, S, CH₂, C═O, NH, CR¹²R¹³ and NR¹⁴, CH₂O and CH₂S,    where in the two last-mentioned groups the carbon atom is attached    to the aromatic moiety and the heteroatom O or S is attached to the    partially hydrogenated moiety of the amine;-   R¹² and R¹³ are each independently of one another selected from the    group consisting of hydrogen, (C₁-C₆)-alkyl and (C₁-C₆)-haloalkyl;-   R¹⁴ is selected from the group consisting of hydrogen, (C₁-C₆)-alkyl    and (C₁-C₆)-haloalkyl; and-   n represents the running number 0, 1 or 2.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The furano-/thienocycloalkylamino-2-pyrimidine derivatives of theformula (I) according to the invention differ from the herbicides with2,4-diaminopyrimidine structure known from the documents EP 0523533 A1,WO 2010/076009 and WO 2010/076010 by the specificfurano-/thienocycloalkylamino substituents in the 2-position of thepyrimidine.

As well as a good profile of efficacy and good crop plant compatibility,the compounds of the formula (I) are notable for their inexpensivepreparation, since the substances of the invention can be prepared frominexpensive and readily available precursors by inexpensive processes.It is therefore possible to dispense with the use of intermediates thatare costly and difficult to obtain.

Compounds of the formula (I) are distinguished in particular by goodcrop plant compatibility in soybeans.

There follows a description of preferred, particularly preferred andvery particularly preferred definitions of each of the individualsubstituents. The other substituents of the general formula (I) whichare not specified hereinafter have the definition given above. The samealso applies to the running number n, meaning that the running number nin the embodiments which follow is 0, 1 or 2.

A first embodiment of the present invention encompasses compounds of thegeneral formula (I) in which

-   A¹, A² and A³ preferably each independently of one another are    selected from the group consisting of S, CR⁹, CR¹⁰ and CR¹¹, where    exactly one atom of A¹, A² and A³ represents S.

In a second embodiment of the present invention encompasses compounds ofthe general formula (I) in which

-   R⁹, R¹⁰ and R¹¹ preferably each independently of one another are    selected from the group consisting of hydrogen, halogen and    (C₁-C₆)-alkyl, and-   R⁹, R¹⁰ and R¹¹ particularly preferably each independently of one    another are selected from the group consisting of hydrogen, chlorine    and (C₁-C₆)-alkyl; and in which-   R⁹, R¹⁰ and R¹¹ even more preferably each independently of one    another are selected from the group consisting of hydrogen and    methyl, and in which-   most preferably exactly one radical R⁹, R¹⁰ or R¹¹ represents methyl    and the other two radicals represent hydrogen.

In a third embodiment of the present invention encompasses compounds ofthe general formula (I) in which

-   A¹, A² and A³ preferably each independently of one another are    selected from the group consisting of O, S, CR⁹, CR¹⁰ and CR¹¹,    where exactly one atom of A¹, A² and A³ represents O or S, and-   R⁹, R¹⁰ and R¹¹ each independently of one another are selected from    the group consisting of hydrogen, chlorine and (C₁-C₃)-alkyl; and-   A¹, A² and A³ particularly preferably each independently of one    another are selected from the group consisting of S, CR⁹, CR¹⁰ and    CR¹¹, where exactly one atom of A¹, A² and A³ represents S, and-   R⁹, R¹⁰ and R¹¹ each independently of one another are selected from    the group consisting of hydrogen and (C₁-C₃)-alkyl, and-   A¹, A² and A³ very particularly preferably each independently of one    another are selected from the group consisting of S, CR⁹, CR¹⁰ and    CR¹¹ where exactly one atom of A¹, A² and A³ is S, and-   R⁹, R¹⁰, and R¹¹ each independently of one another are selected from    the group consisting of hydrogen and methyl, and most preferably    exactly one radical R⁹, R¹⁰ or R¹¹ represents methyl and the other    two radicals represent hydrogen.

A fourth embodiment of the present invention encompasses compounds ofthe general formula (I) in which

-   R¹ and R² preferably each independently of one another are selected    from the group consisting of halogen, hydroxy, nitro, amino, cyano,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl,    (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl and    (C₁-C₆)-haloalkylsulfonyl; and-   R³ preferably each independently of one another is selected from the    group consisting of hydrogen, halogen, hydroxy, nitro, amino, cyano,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl,    (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl and    (C₁-C₆)-haloalkylsulfonyl; and-   R¹ and R² more preferably each independently of one another are    selected from the group consisting of amino, trifluoromethyl,    (C₁-C₃)-alkyl, (C₁-C₆)-alkylsulfonyl; and in which-   R³ more preferably each independently of one another is selected    from the group consisting of hydrogen, amino, trifluoromethyl,    (C₁-C₃)-alkyl, (C₁-C₆)-alkylsulfonyl; and in which-   R¹ and R² particularly preferably each independently of one another    are selected from the group consisting of amino, trifluoromethyl,    methyl and methylsulfonyl, and in which-   R³ particularly preferably each independently of one another is    selected from the group consisting of hydrogen, amino,    trifluoromethyl, methyl and methylsulfonyl, and in which-   R¹, R² and R³ most preferably are each different from one another    and R¹=amino, R²=trifluoromethyl or methylsulfonyl, and R³=hydrogen    or methyl; or-   R¹ is attached to R² via a bond, preferably resulting in a 5- or    6-membered partially hydrogenated carbocycle or heterocycle having    at least one heteroatom selected from the group consisting of N, O,    S and P, which carbocycle or heterocycle is optionally substituted    by one or more substituents selected from the group consisting of    hydroxy, ═O, ═N—O—H, ═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl,    phenyl, phenyl substituted by one or more identical or different    halogen atoms, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl and    (C₁-C₆)-haloalkyl, and-   R³ is selected from the group consisting of hydrogen, amino, methyl    and trifluoromethyl; or-   R¹ is attached to R² via a bond, particularly preferably resulting    in a cyclohexyl ring which is optionally substituted by one or more    substituents selected from the group consisting of hydroxy, ═O,    ═N—O—H, ═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl    substituted by one or more identical or different halogen atoms,    (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl and (C₁-C₆)-haloalkyl, and very    particularly preferably by an oxo group, and-   R³ represents hydrogen, amino or methyl; or-   R¹ is attached to R² via a bond, particularly preferably resulting    in a 6-membered partially hydrogenated heterocycle having one sulfur    atom, which heterocycle is optionally substituted by one or more    substituents selected from the group consisting of hydroxy, ═O,    ═N—O—H, ═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl    substituted by one or more identical or different halogen atoms,    (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl and (C₁-C₆)-haloalkyl, and the    sulfur atom is very preferably substituted by two oxo groups, and-   R³ represents hydrogen, amino or methyl.

A fifth embodiment of the present invention encompasses compounds of thegeneral formula (I) in which

-   R⁴ particularly preferably is selected from the group consisting of    hydrogen, CH₃, CH₂CH₂OCH₃, COOCH₃ and CONH₂; and-   R⁴ very particularly preferably is selected from the group    consisting of hydrogen, CH₃, COOCH₃; and in which-   R⁴ most preferably represents hydrogen.

A sixth embodiment of the present invention encompasses compounds of thegeneral formula (I) in which

-   R⁵ and R⁶ each independently of one another are preferably selected    from the group consisting of hydrogen, hydroxy, (C₁-C₆)-alkyl,    (C₁-C₆)-alkylphenyl and (C₁-C₆)-alkoxy; and-   R⁵ and R⁶ each independently of one another are particularly    preferably selected from the group consisting of hydrogen,    (C₁-C₆)-alkyl and (C₁-C₆)-alkoxy;-   R⁵ and R⁶ each independently of one another are very particularly    preferably selected from the group consisting of hydrogen,    (C₁-C₃)-alkyl and (C₁-C₆)-alkoxy; and in which-   R⁵ and R⁶ each independently of one another are most preferably    hydrogen or methyl.

In the seventh embodiment, it is especially preferred when at least oneof the radical R⁵ and R⁶ represents hydrogen. In other words, when atleast one of the radicals R⁵ and R⁶ represents hydrogen and the otherradical R⁵ and R⁶ does not represent hydrogen, in particular(C₁-C₆)-alkyl, preferably CH₃.

An eighth embodiment of the present invention encompasses compounds ofthe general formula (I) in which

-   R⁷ and R⁸ each independently of one another are preferably selected    from the group consisting of hydrogen, (C₁-C₆)-alkyl and    (C₆-C₁₄)-aryl;-   R⁷ and R⁸ each independently of one another are particularly    preferably selected from the group consisting of hydrogen, methyl    and phenyl; and in which-   R⁷ and R⁸ very particularly preferably each represent hydrogen or    methyl.

A ninth embodiment of the present invention encompasses compounds of thegeneral formula (I) in which

-   X particularly preferably represents a bond (if n=1 or 2) or is    selected from the group consisting of O, S, CH₂, C═O, NH, CHCH₃,    NCH₃, C(CH₃)₂, OCH₂ and SCH₂, where in the two last-mentioned groups    the carbon atom is attached to the aromatic moiety and the    heteroatom O or S is attached to the partially hydrogenated moiety    of the amine; and-   X very preferably represents a bond (if n=1 or 2), or CH₂ or O.

A tenth embodiment of the present invention encompasses compounds of thegeneral formula (I) in which the running number n is preferably 1 or 2.In a very particularly preferred embodiment (1), the running number n=2and X represents a bond or (2) the running number n=1 and X representsCH₂, (3) or the running number n=1 and X represents a bond, such that inall three cases (1) to (3) a 5- or 6-membered ring is formed in eachcase.

In the context of the present invention, it is possible to combine theindividual preferred, more preferred and even more preferred definitionsof the substituents R¹ to R¹⁴, A and X with one another as desired,where the running number n is 0, 1 or 2, preferably 1 or 2.

This means that the present invention encompasses compounds of thegeneral formula (I) in which, for example, the substituent R¹ has apreferred definition and the substituents R² to R¹⁴ have the generaldefinition or else the substituent R² has a preferred definition, thesubstituent R³ has a particularly preferred or very particularlypreferred definition and the remaining substituents have a generaldefinition.

Three of these combinations of the definitions given above for thesubstituents R¹ to R¹⁴, A and X are elucidated by way of examplehereinafter and each are disclosed as further embodiments:

-   -   combination of the definitions each referred to above as being        particularly preferred for the substituents R¹ to R¹¹, A and X        (eleventh embodiment),    -   combination of the definitions each referred to above as being        very particularly preferred for the substituents R¹ to R¹¹, A        and X (twelfth embodiment), and    -   combination of the definitions referred to above as being very        particularly preferred for the substituents R¹ to R¹¹ and X        (thirteenth embodiment),

The aforementioned further embodiments that are based on thecombinations of the substituents are disclosed explicitly hereinafterfor reasons of clarity:

An eleventh embodiment of the present invention encompasses compounds ofthe general formula (I) in which

-   R¹, R² and R³ each independently of one another are selected from    the group consisting of hydrogen, amino, trifluoromethyl,    (C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl; or-   R¹ is attached to R² via a bond, resulting in a 5- or 6-membered    partially hydrogenated carbocycle or heterocycle having at least one    heteroatom selected from the group consisting of N, O, S and P,    which carbocycle or heterocycle is optionally substituted by one or    more substituents selected from the group consisting of hydroxy, ═O,    ═N—O—H, ═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl    substituted by one or more identical or different halogen atoms,    (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl and (C₁-C₆)-haloalkyl, and-   R³ is selected from the group consisting of hydrogen, methyl,    methylsulfonyl, amino and trifluoromethyl;-   R⁴ is selected from the group consisting of hydrogen, CH₃,    CH₂CH₂OCH₃, COOCH₃ and CONH₂;-   R⁵ and R⁶ each independently of one another are selected from the    group consisting of hydrogen, (C₁-C₃)-alkyl and (C₁-C₆)-alkoxy;-   R⁷ and R⁸ each independently of one another are selected from the    group consisting of hydrogen, (C₁-C₆)-alkyl and (C₆-C₁₄)-aryl;-   A¹, A² and A³ each independently of one another are selected from    the group consisting of S, CR⁹, CR¹⁰ and CR¹¹, where exactly one    atom of A¹, A² and A³ represents S;-   R⁹, R¹⁰ and R¹¹ each independently of one another are selected from    the group consisting of hydrogen, halogen and (C₁-C₆)-alkyl;-   X represents a bond (if n=1 or 2) or is selected from the group    consisting of O, S, CH₂, C═O, NH, CHCH₃, NCH₃, C(CH₃)₂, OCH₂ and    SCH₂, where in the two last-mentioned groups the carbon atom is    attached to the aromatic moiety and the heteroatom O or S is    attached to the partially hydrogenated moiety of the amine; and-   n represents the running number 1 or 2.

A twelfth embodiment of the present invention encompasses compounds ofthe general formula (I) in which

-   R¹, R² and R³ each independently of one another are selected from    the group consisting of hydrogen, amino, trifluoromethyl, methyl and    (C₁-C₃)-alkylsulfonyl; or-   R¹ is attached to R² via a bond, resulting in a cyclohexyl ring    which is optionally substituted by one or more substituents selected    from the group consisting of hydroxy, ═O, ═N—O—H,    ═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl    substituted by one or more halogen atoms, (C₁-C₆)-alkyl,    (C₃-C₆)-cycloalkyl and (C₁-C₃)-haloalkyl, in particular    trifluoromethyl, and-   R³ represents hydrogen, methyl, methylsulfonyl or amino; or-   R¹ is attached to R² via a bond, resulting in a 6-membered partially    hydrogenated heterocycle having a sulfur atom, which heterocycle is    optionally substituted by one or more substituents selected from the    group consisting of hydroxy, ═O, ═N—O—H, ═N—O—(C₁-C₆)-alkyl,    ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl substituted by one or more    halogen atoms, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl and    (C₁-C₃)-haloalkyl, and-   R³ represents hydrogen, methyl, methylsulfonyl or amino;-   R⁴ is selected from the group consisting of hydrogen, CH₃ and    COOCH₃;-   R⁵ and R⁶ each independently of one another are selected from the    group consisting of hydrogen, (C₁-C₆)-alkyl and (C₁-C₆)-alkoxy;-   R⁷ and R⁸ each independently of one another are selected from the    group consisting of hydrogen, methyl and phenyl;-   A¹, A² and A³ each independently of one another are selected from    the group consisting of S, CR⁹, CR¹⁰ and CR¹¹, where exactly one    atom of A¹, A² and A³ represents S;-   R⁹, R¹⁰ and R¹¹ each independently of one another are selected from    the group consisting of hydrogen, chlorine and (C₁-C₃)-alkyl;-   X represents a bond (if n=1 or 2), or CH₂ or 0; and-   n represents the running number 1 or 2.

A thirteenth embodiment of the present invention encompasses compoundsof the general formula (I) in which

-   R¹, R² and R³ are each different than one another and are selected    from the group consisting of hydrogen, amino, trifluoromethyl,    methyl and methylsulfonyl; or-   R¹ is attached to R² via a bond, such that a cyclohexyl ring    optionally substituted by ═O is formed, and-   R³ represents hydrogen, methyl or amino; or-   R¹ is attached to R² via a bond, such that a 6-membered partially    hydrogenated heterocycle having a sulfur atom is formed, which    heterocycle is substituted by 2 oxo groups, and-   R³ represents hydrogen, methyl or amino;-   R⁴ represents hydrogen;-   R⁵ and R⁶ each independently of one another represent hydrogen or    methyl;-   R⁷ and R⁸ each independently of one another represent hydrogen or    methyl;-   A¹, A² and A³ each independently of one another are selected from    the group consisting of S, CR⁹, CR¹⁰ and CR¹¹, where exactly one    atom of A¹, A² and A³ represents S;-   R⁹, R¹⁰, and R¹¹ each independently of one another are selected from    the group consisting of hydrogen and methyl, and preferably exactly    one radical R⁹, R¹⁰ or R¹¹ represents methyl and the other two    radicals represent hydrogen.-   X represents a bond (if n=1 or 2), or CH₂ or 0; and-   n represents the running number 1 or 2.

In the context of the present invention, the compound of the generalformula (I) also includes compounds quaternized on a nitrogen atom by a)protonation, b) alkylation or c) oxidation. In this respect, particularmention may be made of the corresponding N-oxides.

The compounds of the formula (I) are capable of forming salts. Salts maybe formed by the action of a base on those compounds of the formula (I)that bear an acidic hydrogen atom. Examples of suitable bases areorganic amines such as trialkylamines, morpholine, piperidine orpyridine, and the hydroxides, carbonates and hydrogencarbonates ofammonium, alkali metals or alkaline earth metals, especially sodiumhydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,sodium hydrogencarbonate and potassium hydrogencarbonate. These saltsare compounds in which the acidic hydrogen is replaced by anagriculturally suitable cation, for example metal salts, especiallyalkali metal salts or alkaline earth metal salts, in particular sodiumand potassium salts, or else ammonium salts, salts with organic aminesor quaternary ammonium salts, for example with cations of the formula[NRR′R″R′″]⁺ in which R to R′″ each independently of one anotherrepresent an organic radical, in particular alkyl, aryl, aralkyl oralkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts,such as (C₁-C₄)-trialkylsulfonium and (C₁-C₄)-trialkylsulfoxonium salts.

The compounds of the formula (I) can form salts by addition of asuitable inorganic or organic acid, for example mineral acids, forexample HCl, HBr, H₂SO₄, H₃PO₄ or HNO₃, or organic acids, for examplecarboxylic acids such as formic acid, acetic acid, propionic acid,oxalic acid, lactic acid or salicylic acid or sulfonic acids, forexample p-toluenesulfonic acid, onto a basic group, for example amino,alkylamino, dialkylamino, piperidino, morpholino or pyridino. In such acase, these salts will comprise the conjugate base of the acid as theanion.

Suitable substituents present in deprotonated form, such as, forexample, sulfonic acids or carboxylic acids, may form inner salts withgroups which for their part can be protonated, such as amino groups.

The compounds of the formula (I) and their salts are also referred tohereinafter as “compounds (I)” according to the invention or used inaccordance with the invention.

In the general formula (I) and in all the other formulae of the presentinvention, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy,alkylamino, alkylthio, haloalkylthio and the corresponding unsaturatedand/or substituted radicals can in each case be straight-chain orbranched in the carbon skeleton. Unless stated specifically, preferenceis given for these radicals to the lower carbon skeletons, for examplethose having 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, orin the case of unsaturated groups having 2 to 6 carbon atoms, inparticular 2 to 4 carbon atoms. Alkyl radicals, both alone and incomposite definitions such as alkoxy, haloalkyl, etc., are, for example,methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, tert-butyl or2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and1,4-dimethylpentyl; alkenyl and alkynyl radicals have the definition ofthe possible unsaturated radicals corresponding to the alkyl radicals;where at least one double bond or triple bond is present, preferably onedouble bond or triple bond, respectively. Alkenyl is, for example,vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and1-methylbut-2-en-1-yl; alkynyl is, for example, ethynyl, propargyl,but-2-yn-1-yl, but-3-yn-1-yl and 1-methylbut-3-yn-1-yl.

Cycloalkyl groups are, for example, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. The cycloalkylgroups can be present in bi- or tricyclic form.

If haloalkyl groups and haloalkyl radicals of haloalkoxy, haloalkylthio,haloalkenyl, haloalkynyl etc. are stated, the lower carbon skeletons ofthese radicals having, for example, 1 to 6 carbon atoms or 2 to 6 carbonatoms, in particular 1 to 4 carbon atoms or preferably 2 to 4 carbonatoms, and the corresponding unsaturated and/or substituted radicals arein each case straight-chain or branched in the carbon skeleton. Examplesare difluoromethyl, 2,2,2-trifluoroethyl, trifluoroallyl,1-chloroprop-1-yl-3-yl.

Alkylene groups in these radicals are the lower carbon skeletons, forexample those having 1 to 10 carbon atoms, in particular 1 to 6 carbonatoms, or preferably 2 to 4 carbon atoms, and also the correspondingunsaturated and/or substituted radicals in the carbon skeleton which mayin each case be straight-chain or branched. Examples are methylene,ethylene, n- and isopropylene and n-, s-, iso-, t-butylene.

Hydroxyalkyl groups in these radicals are the lower carbon skeletons,for example those having 1 to 6 carbon atoms, in particular 1 to 4carbon atoms, and also the corresponding unsaturated and/or substitutedradicals in the carbon skeleton which may in each case be straight-chainor branched. Examples of these are 1,2-dihydroxyethyl and3-hydroxypropyl.

Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyland -alkynyl are alkyl, alkenyl and alkynyl partly or fully substitutedby halogen, preferably by fluorine, chlorine or bromine, especially byfluorine and/or chlorine, for example monohaloalkyl, perhaloalkyl, CF₃,CF₂Cl, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃, CHCl₂, CH₂CH₂Cl; haloalkoxyis, for example, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ and OCH₂CH₂Cl; thesame correspondingly applies to haloalkenyl and otherhalogen-substituted radicals.

Aryl is a monocyclic, bicyclic or polycyclic aromatic system, forexample phenyl or naphthyl, preferably phenyl.

A heterocycle is a carbocycle in which at least one carbon atom isreplaced by a heteroatom, preferably by a heteroatom from the groupconsisting of N, O, S and P.

The heterocyclic ring preferably contains 5 to 7 ring atoms, inparticular 5 to 6, and one or more, preferably 1 to 2, in particular 1heteroatom in the heterocyclic ring, preferably from the groupconsisting of N, O and S, particularly preferably O or S and mostpreferably S.

The heterocycles are optionally substituted by one or more substituentsselected from the group consisting of hydroxy, ═O, ═N—O—H,═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl substitutedby one or more identical or different halogen atoms, (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl and (C₁-C₆)-haloalkyl.

Primarily for reasons of higher herbicidal activity, better selectivityand/or better preparability, compounds of the general formula (I)according to the invention or the agrochemical salts or quaternary Nderivatives thereof that are of particular interest are those in whichindividual radicals have one of the preferred definitions alreadyspecified or specified below, or especially those in which one or moreof the preferred definitions already specified or specified below occurin combination.

The abovementioned general or preferred radical definitions apply bothto the end products of the general formula (I) and, correspondingly, tothe starting materials and intermediates required in each case for thepreparation. These radical definitions can be exchanged for one anotheras desired, i.e. including combinations between the given preferredranges.

If tautomers are possible, the form described embraces all possibletautomeric structures. As shown below, when, for example R¹ and/orR³=hydroxy, the possible keto tautomers are likewise embraced; thisapplies analogously to amino and any imino tautomers.

The present compounds of the general formula (I) have, at the bindingsite to the aminopyrimidine, a chiral carbon atom which, in thestructure shown below, is indicated by the marker (*):

According to the rules of Cahn, Ingold and Prelog (CIP rules), thiscarbon atom can have either an (R) configuration or an (S)configuration.

The present invention encompasses compounds of the general formula (I)both with (S) and with (R) configuration, meaning that the presentinvention encompasses the compounds of the general formula (I) in whichthe carbon atom in question has

-   -   (1) an (R) configuration; or    -   (2) an (S) configuration.

In addition, the scope of the present invention also encompasses

-   -   (3) any mixtures of compounds of the general formula (I) having        an (R) configuration (compounds of the general formula (I-(R))        with compounds of the general formula (I) having an (S)        configuration (compounds of the general formula (I-(S)),        with a racemic mixture of the compounds of the general        formula (I) having (R) and (S) configuration likewise being        embraced by the present invention.

However, within the context of the present invention, preference isgiven to using particularly compounds of the general formula (I) having(R) configuration with a selectivity of 60 to 100%, preferably 80 to100%, especially 90 to 100%, even more preferably 95 to 100%, where theparticular (R) compound is present with an enantioselectivity of in eachcase more than 50% ee, preferably 60 to 100% ee, especially 80 to 100%ee, very particularly 90 to 100% ee, most preferably 95 to 100% ee,based on the total content of (R) compound in question.

Accordingly, the present invention relates especially to compounds ofthe general formula (I*) in which the stereochemical configuration onthe carbon atom marked by (*) is present with a stereochemical purity of60 to 100% (R), preferably 80 to 100% (R), especially 90 to 100% (R),very particularly 95 to 100% (R).

Taking into account the Cahn, Ingold and Prelog rules, at the carbonatom marked (*) there may also be a situation in which, owing to thepriority of the substituent in question, the (S) configuration ispreferred at the carbon atom marked (*). This is the case, for example,when the radicals R⁴ and/or R⁵ correspond to a C₁-C₆-alkoxy radical.

Accordingly, within the context of the present invention, preference isgiven especially to compounds of the general formula (I) whose spatialarrangement corresponds to that of the compounds of the general formula(I) where R⁴ and R⁵=hydrogen having the (R) configuration, with aselectivity of 60 to 100%, preferably 80 to 100%, especially 90 to 100%,even more preferably 95 to 100%, where the respective (R)-analogouscompound is present with an enantioselectivity of in each case more than50% ee, preferably 60 to 100% ee, especially 80 to 100% ee, even morepreferably 90 to 100% ee, most preferably 95 to 100% ee, based on thetotal content of (R) analogous compound in question Accordingly, thepresent invention relates especially to compounds of the general formula(I) in which the stereochemical configuration on the carbon atom markedby (*) is present with a stereochemical purity of 60 to 100% (R or Ranalog), preferably 80 to 100% (R or R analog), especially 90 to 100% (Ror R analog), very particularly 95 to 100% (R or R analog).

In particular, the compounds of the general formula (I) according to theinvention may have further centers of chirality at the carbon atomsmarked (**) and (***):

In the context of the present invention, any stereochemicalconfigurations are possible at the carbon atoms marked (*), (**) and(***):

Configuration Configuration Configuration of carbon atom of carbon atomof carbon atom (*) (**) (***) R R R R R S R S R S R R R S S S R S S S RS S S

In addition, depending on the respective radicals chosen, furtherstereoelements may be present in the compounds of the general formula(I) according to the invention.

If, for example, one or more alkenyl groups are present, diastereomers(Z and E isomers) may occur.

If, for example, one or more asymmetric carbon atoms are present,enantiomers and diastereomers may occur.

Corresponding stereoisomers can be obtained from the mixtures obtainedin the preparation by customary separation methods, for example bychromatographic separation processes. It is likewise possible toselectively prepare stereoisomers by using stereoselective reactionswith use of optically active starting materials and/or auxiliaries. Theinvention thus also relates to all stereoisomers which are encompassedby the general formula (I) but are not shown in their specificstereomeric form, and to mixtures thereof.

The possible combinations of the various substituents of the generalformula (I) should be understood such that the general principles of theconstruction of chemical compounds have to be observed, i.e. the formula(I) does not encompass any compounds known by the person skilled in theart to be chemically impossible.

Examples of the compounds of the general formula (I) are shown below intabular form.

Tables 1 and 2 below specify the substituents defined in general termsin formula (I). In these tables:

-   -   “StNR⁴” represents the stereochemical arrangement on the carbon        atom to which NH and R⁴ are bonded,    -   “StR⁵R⁶” and “StR⁷R⁸” analogously represent the carbon atoms to        which the respective substituents are bonded,    -   the bond of the substituents is on the left in each case,    -   if two binding sites are reported for X, the left-hand bond is        bonded to the aromatic ring and the right-hand bond to the        hydrogenated moiety of the bicyclic amine,    -   a hyphen “-” denotes a direct bond, and    -   if n=0, the table does not contain an entry in the corresponding        field for R⁶ and R⁷.

TABLE 1 No. R¹ R² R³ R⁴ StNR⁴ R⁵ 1. —NH₂ —CF₃ —H —H rac —H 2. —NH₂ —CF₃—H —H rac —H 3. —NH₂ —SO₂—CH₃ —H —H rac —H 4. —NH₂ —SO₂—CH₃ —H —H rac —H5. T1 —CF₃ —H —H rac —H 6. —NH₂ —SO₂—CH₃ —H —H rac —H 7. —NH₂ —CF₃ —H —Hrac —H 8. —(CH₂)₃C(═O)— —H —H rac —H 9. —(CH₂)₃C(═O)— —H —H rac —H 10.—OCH₃ —CF₃ —H —H rac —H 11. —NH₂ —CF₃ —H —H rac —H 12. —NH₂ —F —H —H rac—H 13. —NH₂ —SO₂—CH₃ —H —H rac —H 14. —NH₂ —CClF₂ —H —H rac —H 15. —NH₂—SO₂—CH₃ —H —H rac —H 16. —NH₂ —SO₂—CH₃ —Cl —H rac —H 17. —NH₂ —SO₂—CH₃—H —H rac —CH₃ 18. —NH₂ —SO₂—CH₃ —H —H rac —H 19. —NH₂ —SO₂—CH₃ —H —Hrac —H 20. —NH₂ —SO₂—CH₃ —H —H rac —H 21. —NH₂ —CF₃ —H —H rac —H 22.—NH₂ —CF₃ —H —H rac —H 23. —NH₂ —SO₂—CH₃ —H —H rac —H 24. —NH₂ —SO₂—CH₃—H —H R —H 25. —NH₂ —SO₂—CH₃ —H —H rac —H 26. —NH₂ —CF₂H —H —H rac —H27. —NH₂ —S(═O), (═NH)—Ph —H —H rac —H 28. —NH₂ —CF₃ —H —H rac —H 29.—NH₂ —CF₃ —H —H rac —H 30. —NH₂ —C(═O)CClF₂ —H —H rac —H 31. —NH₂ —CF₃—H —H rac —H 32. —NH₂ —NO₂ —H —H rac —H 33. —NH₂ —SO₂—CH₃ —H —H rac —H34. —NH₂ —CF₃ —H —H rac —H 35. —NH₂ —SO—CH₃ —CF₃ —H rac —H 36. —NH₂—SO₂-cyclopropyl —H —H rac —H 37. —NH₂ —SO₂—(CH₂)₂—CH₃ —H —H rac —H 38.—NH₂ —SO₂—NH—CH₂—(4-F—Ph) —H —H rac —H 39. —NH₂ —SO—CH₃ —Cl —H rac —H40. —NH₂ —NO₂ —H —H rac —H 41. —NH₂ —CF₃ —H —H rac —H 42. —NH₂ —SO₂—CH₃—H —H rac —H 43. —NH₂ —CF₃ —H —H rac —H 44. —(CH₂)₃—S(═O)₂— —H —H R —H45. —NH₂ —SO₂—CH₃ —H —H rac —H 46. —NH₂ —CF₃ —H —H R —H 47. —NH₂ —CF₃ —H—H R —H 48. —NH₂ —CF₃ —H —H rac —H 49. —NH₂ —CN —H —H rac —H 50. —NH₂—SO₂—CH₃ —H —H rac —H 51. —NH₂ —CF₃ —H —H rac —CH₃ 52. —NH₂ —CN —H —Hrac —H 53. —NH₂ —SO₂—CH₃ —H —H rac —H 54. —(CH₂)₃—C(═O)— —H —H rac —H55. —NH₂ —CF₃ —H —H rac —H 56. —NH₂ —CN —H —H rac —H 57. —NH₂ —CN —H —Hrac —H 58. —NH₂ —SO₂—CH₃ —H —H rac —H 59. —NH₂ —SO₂—CH₃ —H —H rac —H 60.—CH₃ —C(═O)—CH₃ —H —H rac —H 61. —NH₂ —CF₃ —H —H rac —H 62. —NH₂—SO₂—CH₃ —H —H rac —H 63. —NH₂ —SO₂—CH—(CH₃)₂ —H —H rac —H 64. —NH₂ —CN—CH₃ —H rac —H 65. —NH₂ —CF₃ —H —H rac —H 66. —NH₂ —SO₂—(CH₂)₃—OCH₃ —H—H rac —H 67. —NH₂ —CF₃ —H —H rac —COOCH₃ 68. —(CH₂)₃—S(═O)₂— —H —H rac—H 69. —NH₂ —SO₂—CH₃ —H —H rac —H 70. —NH₂ —CF₃ —H —H rac —H 71. —CH₃—C(═O)—CH₃ —H —H R —H 72. —NH₂ —C(═O)—CF₃ —H —H rac —H 73.—(CH₂)₃—S(═O)₂— —H —H R —H 74. —NH₂ —CN —CH₃ —H rac —H 75. T2 —CF₃ —H —Hrac —H 76. —NH₂ —SO₂—C(CH₃)₃ —H —H rac —H 77. —NH₂ —SO₂—C(CH₃)₃ —H —Hrac —H 78. —NH₂ —CF₃ —H —H rac —H 79. T3 —CF₃ —H —H rac —H 80. —CH₃—S—CF₃ —H —H rac —H 81. T4 —CF₃ —H —H rac —H 82. T5 —CF₃ —H —H R —H 83.—NH₂ —CN —CH₂—CH₃ —H rac —H 84. —NH₂ —NO₂ —H —H rac —H 85. —NH₂ —CF₂—CH₃—H —H rac —H 86. —NHCOCH₃ —CF₃ —H —H rac —H 87. —NHCOC(CH₃)₃ —CF₃ —H —Hrac —H 88. —NHCOCF₃ —CF₃ —H —H rac —H 89. —NHCOPh —CF₃ —H —H rac —H 90.—NHCO-(3-MeO—Ph) —CF₃ —H —H rac —H 91. —NHCO-(3,5-di-Cl—Ph) —CF₃ —H —Hrac —H 92. —NHCOCH₂CH₂OCH₃ —CF₃ —H —H rac —H 93. —NHCOCH₂OCH₃ —CF₃ —H —Hrac —H 94. —NHCO-(3-CF₃—Ph) —CF₃ —H —H rac —H 95. —NHCO-(3,5-diCH₃—Ph)—CF₃ —H —H rac —H 96. —N═CH—N(CH₃)₂ —CF₃ —H —H rac —H 97.—N═CCH₃—N(CH₃)₂ —CF₃ —H —H rac —H 98. T6 —CF₃ —H —H rac —H 99. T7 —CF₃—H —H rac —H 100. —NHOH —CF₃ —H —H rac —H 101. —OH —CF₃ —H —H rac —H102. —NH—NH₂ —CF₃ —H —H rac —H 103. —NHOCH₃ —CF₃ —H —H rac —H 104.—NHOCH₂CH₃ —CF₃ —H —H rac —H 105. —NH—NHCOCH₃ —CF₃ —H —H rac —H 106.-triazol-1yl- —CF₃ —H —H rac —H 107. —O-(4-F—Ph) —CF₃ —H —H rac —H 108.—NH—O—Ph —CF₃ —H —H rac —H 109. —O-(3,5-diCH₃—Ph) —CF₃ —H —H rac —H 110.—O-(4-CH₃—O—Ph) —CF₃ —H —H rac —H 111. —OCH₂(4-F—Ph) —CF₃ —H —H rac —H112. —OCO(4-F—Ph) —CF₃ —H —H rac —H 113. —NHCO(4-F—Ph) —CF₃ —H —H rac —H114. —COOCH₃ —Cl —H —H R —H 115. —CF₃ —CH₃ —H —H R —H 116. —CH₃ —CH₃ —H—H R —H 117. —(CH₂)₄— —H —H R —H 118. —(CH₂)₄— —CF₃ —H R —H 119.—(CH₂)₃C(═O)— —H —H R —H 120. —(CH₂)₃C(<Z>═NOH)— —H —H R —H 121.—(CH₂)₃C(<E>═NOH)— —H —H R —H 122. —(CH₂)₃C(<Z>═NOCH₃)— —H —H R —H 123.—(CH₂)₃C(<Z>═NOH)— —NH₂ —H R —H 124. —(CH₂)₃C(═O)— —NH₂ —H R —H 125.—NH—(CH₂)₂C(═O)— —H —H R —H 126. —NH—CH═CH—C(═O)— —H —H R —H 127.—NCH₃—(CH₂)₂C(═O)— —H —H R —H 128. —N(4-F—Ph)—CH═CH—C(═O)— —H —H R —H129. —NCH₃—C(—COOCH₃)═CH—C(═O)— —H —H R —H 130. —NH—C(—COOCH₃)═CH—C(═O)——H —H R —H 131. —N(CH₃)₂ —F —H —H R —H 132. —N(CH₃)—(CH₂)₃— —H —H R —H133. —NH₂ —F —H —H R —H 134. —NH₂ —CH₃ —H —H R —H 135. —NH₂ —CH₃ —CH₃ —HR —H 136. —NH₂ —(CH₂)₄— —H R —H 137. —CH₂—O—CH₂—C(═O)— —H —H R —H 138.—CH₂—O—CH₂—C(═O)— —H —H R —H 139. —CH₂—CH(CH₃)—CH₂—C(═O)— —H —H R —H140. —CH₂—CH(Ph)—CH₂—C(═O)— —H —H R —H 141. —CH₂—CH(4-F—Ph)—CH₂—C(═O)——H —H R —H 142. —CH₂—CH(4-F—Ph)—CH₂—C(<E>═NOH)— —H —H R —H 143.—CH₂—CH(4-F—Ph)—CH₂—C(<Z>═NOCH₃)— —H —H R —H 144. —NH₂ —CF₂—CF₃ —H —Hrac —H 145. —NH₂ —C≡CH —H —H rac —H 146. —NH₂ —C≡CCH₃ —H —H rac —H 147.—NH₂ —C≡CPh —H —H rac —H 148. —NH₂ —C≡CCH₂—OH —H —H rac —H 149. —NH₂—C(═O)—CH₂—CH₃ —H —H rac —H 150. —NH₂ —C(═O)—CH₃ —H —H rac —H 151.—CH₂—CH₃ —C(═O)—CH₂—CH₃ —H —H rac —H 152. —N(CH₃)₂ —CF₃ —H —H rac —H153. —NH₂ —C(═O)—CH₂—O—CH₃ —H —H R —H 154. —N(CH₃)₂ —CF₃ —H —H R —H 155.—N(CH₃)₂ —CF₃ —H —H rac —H 156. —N(CH₃)₂ —C(═O)—CH₃ —H —H R —H 157.—N(CH₃)₂ —C(═O)—CH₃ —H —H R —H 158. —CH₃ —C(<E>═NOH)—CH₃ —H —H R —H 159.—CH₃ —C(<E>═NOCH₃)—CH₃ —H —H R —H 160. —CH₃ —C(<E>═NOPh)—CH₃ —H —H R —H161. —CH₃ —CH(—OH)—CH₃ —H —H R —H 162. —CH₃ —CFH—CH₃ —H —H R —H 163.—CH₃ —CH(—OCH₂—Ph)—CH₃ —H —H rac —H 164. —CH₃ —CH(—OCH₂—4-F—Ph)—CH₃ —H—H R —H 165. —CH₃ —CH(—OCH₂—4-OCH₃—Ph)—CH₃ —H —H R —H 166. —NH₂—CH(—OCH₂—4-OCH₃—Ph)—CH₃ —H —H R —H 167. —NH₂ —CH(—OH)—CH₃ —H —H R —H168. —NH₂ —CH(—OH)—CH₃ —H —H R —H 169. —NH₂ —CFH—CH₃ —H —H R —H 170.—NH₂ —Cl —H —H R —H 171. —NH₂ —Cl —H —H R —H 172. —NH₂ —Br —H —H R —H173. —NH₂ —I —H —H R —H 174. —NH₂ —COOCH₃ —H —H R —H 175. CH₃—C(═O)—N(NCH₃)2 —H —H R —H 176. —CH3 —C(═O)—OCH₃ —H —H R —H 177. —CH3—C(═O)—NH₂ —H —H R —H 178. —NH₂ —C(═O)—N—(CH₃)₂ —H —H R —H 179. —NHCH₃—CF₃ —H —H rac —H 180. CH₃ —CF₃ —H —H R —H 181. —CH₃ —C(═O)—CH₃ —H —H R—H 182. —CH₃ —C(═O)—CH₃ —H —H R —H 183. —CH₃ —C(<E>═NOH)—CH₃ —H —H R —H184. —(CH₂)₂—C(<Z>═NOH)— —H —H R —H 185. —(CH₂)₂—C(═O)— —H —H R —H 186.—(CH₂)₂—C(═O)— —H —H R —H 187. —OCH₃ —S—CF₃ —H —H R —H 188. —CH₃ —S—CF₃—H —H R —H 189. —NH₂ —S—CF₃ —H —H R —H 190. —(CH₂)—C(═O)—CH₂— —H —H R —H191. —C(═O)—(CH₂)₃— —H —H R —H 192. —C(<E>═NOH)—(CH₂)₃— —H —H R —H 193.—NH₂ —SO₂—CH₃ —H —H R —H 194. —NH₂ —SO₂—CH₃ —H —H R —H 195. —NH₂—SO₂—CH₃ —H —H R —H 196. —NH₂ —SO₂—CH₃ —H —H rac —CH₃ 197. —NH₂ —Cl —H—H rac —CH₂—CH₃ 198. —NH₂ —CF₃ —H —H rac -spiro-cyclopropyl 199. —NH₂—SO₂—CH₃ —NH₂ —H rac —H 200. —NH₂ —SO₂—CH₃ —NH₂ —H R —H 201. —NH₂—SO₂—CH₃ —H —CH₃ rac —H 202. —NH₂ —CF₃ —H —CH₃ rac —H 203. —NH₂ —SO₂—CH₃—H —CN rac —H 204. —NH₂ —SO₂—CH₃ —H —COOCH₃ rac —H 205. —NH₂ —SO₂—CH₃ —HR —CH₃ 206. —NH₂ —CF₃ —H R —CH₃ 207. —NH₂ —CF₃ —H —H rac —H 208. —NH₂—CF₃ —H —H rac —H 209. —NH₂ —SO—CH₃ —H —H rac —H 210. —NH₂ —SO—CH₃ —H —Hrac —H 211. —CF₃ —CN —H —H R —H 212. —CF₃ —CN —H —H rac —H 213. —NH₂—CF₃ —H —H rac —H 214. -T8 —CF₃ —H —H rac —H 215. —NH₂ —CF₃ —H —H rac —H216. —CH₃ —CF₃ —H —H rac —H 217. —CH₃ —CF₃ —H —H rac —H 218. —CH₃ —CF₃—H —H rac —H 219. —CH₃ —CF₃ —H —H rac —H 220. —CH₃ —CF₃ —H —H R —H 221.—CF₃ —COOCH₃ —H —H rac —H 222. —NH₂ —Cl —CF₃ —H rac —H 223. —CH₃ —F —H—H R —H 224. —OCH₃ —F —H —H rac —H 225. —OCH₃ —Cl —H —H R —H 226. —OCH₃—Cl —H —H rac —H 227. —OCH₃ —Br —H —H R —H 228. —OCH₃ —Br —H —H rac —H229. —OCH₃ —C≡CSi(CH₃)₃ —H —H R —H 230. —OCH₃ —C≡CH —H —H R —H 231.—OCH₃ —C≡CCH₂CH₂CH₂CH₃ —H —H R —H 232. —OCH₃ —C≡CSi(CH₃)₃ —H —H rac —H233. —OCH₃ —C≡CH —H —H rac —H 234. —OCH₃ —C≡CCH₂CH₂CH₂CH₃ —H —H rac —H235. —CH₃ —C(═O)—OCH₂CH₃ —H —H R —H 236. —CH₃ —C(═O)N(CH₃)₂ OH —H —H R—H 237. —CH₃ —C(═O)—N(CH₃)CH₂—4-F—Ph —H —H R —H 238. —CH₃ —C(═O)-azepine—H —H R —H 239. —CH₃ —C(═O)—N(CH₃)CH₂—2-F—Ph —H —H R —H 240. —CH₃—C(═O)—OCH₂CH₃ —H —H rac —H 241. —CH₃ —C(═O)NHCH₃ —H —H rac —H 242. —CH₃—C(═O)-azepine —H —H rac —H 243. —CH₃ —C(═O)—N(CH₃)CH₂—4-F—Ph —H —H rac—H 244. —CH₃ —C(═O)—N(CH₃)CH₂—2-F—Ph —H —H rac —H 245. —NH₂ —CF₃ —H —CH₃rac —H 246. —NH₂ —SO₂—CH₃ —NH₂ —CH₃ rac —H 247. —NH₂ —SO₂—CH₃ —H —H rac—CH₃ 248. —NH₂ —CF₃ —H —H rac —H 249. —NH₂ —CF₃ —H —H rac —H 250. —NH₂—CF₃ —H —H rac —H 251. —(CH₂)₃C(═O)— —H —H rac —H 252.—(CH₂)₃C(═N<Z>OH)— —H —H rac —H 253. —(CH₂)₃C(═N<E>OH)— —H —H rac —H254. —(CH₂)₃C(═N<E>OCH₃)— —H —H rac —H 255. —(CH₂)₃C(═N<Z>OCH₃)— —H —Hrac —H 256. —NH₂ —CF₃ —H —H rac —H 257. —NH₂ —CF₃ —H —H rac —H 258. —CH₃—COCH₃ —H —H rac —H 259. —CH₃ —C(═N<Z>OH)CH₃ —H —H rac —H 260. —CH₃—C(═N<E>OH)CH₃ —H —H rac —H 261. —CH₃ —C(═N<Z>OCH₃)CH₃ —H —H rac —H 262.—CH₃ —C(═N<E>OCH₃)CH₃ —H —H rac —H 263. —C(CH₃)═CH—C(═O)—N(-T9)- —H —Hrac —H 264. —NH₂ —SO—CH₃ —CF₂H —H rac —H 265. —NH₂ -3-F—Ph —H —H rac —H266. —NH₂ —C(═O)—NHCH₃ —H —H rac —H 267. —NH₂ —C(═O)—NH₂ —H —H rac —H268. —NH₂ —C(═O)—CH₃ CF₃ —H rac —H 269. —CF₃ —C(═O)—CH₃ —H —H rac —H270. —OCH₃ —CF₃ —H —H rac —H 271. T10 —CF₃ —H —H rac —H 272. —OCH₃ —CF₃—H —H rac —H 273. T11 —CF₃ —H —H rac —H 274. —OCH₃ —CF₃ —H —H rac —H275. —NH₂ —C(═CH₂)—CF₃ —H —H rac —H 276. —CH₃ —C═N(<Z>—OCH₂CH₃)—CH₃ —H—H rac —H 277. —CH₃ —C(═N(<E>—OCH₂CH₃)—CH₃ —H —H rac —H 278. —CH₃—C(═N(<Z>—OCH₂Ph—CH₃ —H —H rac —H 279. —CH₃ —C(═N(<E>—OCH₂Ph)—CH₃ —H —Hrac —H 280. —NH₂ —Cl —CF₃ —H R —H 281. —NH₂ —Cl —CF₃ —H rac —H 282. —NH₂—CN —H —H R —H 283. —NH₂ —C(═O)—CH₃ —H —H R —H 284. —NH₂ —Br —CHF₂ —Hrac —H 285. —NH₂ —CF₃ —H —H rac —H 286. —NH₂ —C═N(<E>—OH)—CH₃ —H —H R —H287. —NH₂ —SO₂—CH₃ —CHF₂ —H rac —H 288. —NH₂ —C(═N(<E>—OCH(CH₃)₂)—CH₃ —H—H rac —H 289. —NH₂ —H —CHF₂ —H rac —H 290. —NH₂ -T12 —H —H rac —H 291.—NH₂ —C(═N(<Z>—OCH₂Ph)—CH₃ —H —H rac —H 292. —NH₂ —C(═N(<Z>—OCH₃)—CH₃ —H—H rac —H 293. —NH₂ —C(═O)OCH₂—CH₃ —H —H rac —H 294. —NH₂ —Ph-3-CF₃ —H—H rac —H 295. —NH₂ —C(═N(<E>—OCH₃)—CH₃ —H —H rac —H 296. —NH₂ —Ph —H —Hrac —H 297. —NH₂ —Ph-3-Cl —H —H rac —H 298. —NH₂ —SO₂—CH₃ —CF₃ —H rac —H299. —NH₂ -T13 —CHF₂ —H rac —H 300. —NH₂ -T14 —CHF₂ —H rac —H 301. —NH₂—C(═O)—CH₃ —H —H R —H 302. —NH₂ —Ph-3-F —CHF₂ —H rac —H 303. —CH₃—C(═O)—CH₃ —H —H R —H 304. —NH₂ —Ph-3-CH₃ —CHF₂ —H rac —H 305. —NH₂—C(═N(<E>—OCH₂Ph)—CH₃ —H —H rac —H 306. —NH₂ —CH₂OH —H —H R —H 307. —NH₂—Br —CF(CH₃)₂ —H rac —H 308. —NH₂ —Cl —CHFCH₃ —H rac —H 309. —NH₂ —SOCH₃—CHFCH₃ —H rac —H 310. —NH₂ —C(═N(<E>—OCH₃)—CH₃ —H —H rac —H 311. —NH₂—CH₃ —CF(CH₃)₂ —H rac —H 312. —NH₂ —Ph-3-NO₂ —H —H rac —H 313. —NH₂—Ph-3-CN —H —H rac —H 314. —NH₂ —Br —CHF₂ —H rac —H 315. —NH₂ —SO₂—CH₃—CF(CH₃)₂ —H rac —H 316. —NH₂ -T13 —CHFCH₃ —H rac —H 317. —NH₂ —Ph-3-F—CHFCH₃ —H rac —H 318. —NH₂ —SO₂—CH₃ —CHFCH₃ —H rac —H 319. —NH₂ —CN—CF(CH₃)₂ —H rac —H 320. —NH₂ —CN —CHFCH₃ —H rac —H 321. —NH₂ —Ph-3-F—CF(CH₃)₂ —H rac —H 322. —CH₃ —C≡C—Ph-4-CH₂CH₃ —H —H rac —H 323. —NH₂-T13 —CF(CH₃)₂ —H rac —H 324. —CH₃ —C═C—Ph-4-O—CH₃ —H —H rac —H 325.—CF₃ —Cl —H —H R —H 326. —CF₃ —Cl —H —H R —H 327. —CH₃ —C(═O)-T15 —H —Hrac —H 328. —NH₂ —C(═O)H —H —H rac —H 329. —NH₂ —CN —CHF₂ —H rac —H 330.—CH₃ —C(═O)-T16 —H —H rac —H 331. —CH₃ —C(═O)NH-T17 —H —H rac —H 332.—CF₃ —C(═O)T18 —H —H rac —H 333. —CF₃ —C(═O)NH-T17 —H —H rac —H 334.—CF₃ —C(═O)N(CH₃)CH₂—2-F—Ph —H —H rac —H 335. —CF₃ —C(═O)-T16 —H —H rac—H 336. —CF₃ —C(═O)-T15 —H —H rac —H 337. —(CH₂)₃—C(═O)— —H —H rac —H338. —(CH₂)₂—NH—C(═O)— —H —H rac —H 339. —(CH₂)₂—NH—C(═O)— —H —H rac —H340. —(CH₂)₂—NH—C(═O)— —H —H rac —H 341. —NH₂ —C═N(<E>—OH)—CH₃ —H —H rac—H 342. —NH₂ —C(═N(<Z>—OCH(CH₃)₂)—CH₃ —H —H rac —H 343.—NH—(CH₂)₂—C(═O)— —H —H rac —H 344. —NH—CH₂—CH(C(═O)OCH₃)—C(═O)— —H —Hrac —H 345. —N(CH₃)—(CH₂)₂—C(═O)— —H —H rac —H 346.—N(CH₃)—CH₂—CH(C(═O)OCH₃)—C(═O)— —H —H rac —H 347. —N(T19)-(CH₂)₂—C(═O)——H —H rac —H 348. —N(T19)-CH₂—CH(C(═O)OCH₃)—C(═O)— —H —H rac —H 349.—CH₃ —C(═N<Z>OH)CH₃ —H —H R —H 350. —CH₃ —C(═N<E>OH)CH₃ —H —H R —H 351.—Cl —CF₃ —H —H rac —H 352. —NH₂ —C(═N<E> CH₃)CH₃ —H —H R —H No. R⁶StR⁵R⁶ R⁷ R⁸ n StR⁷R⁸ A¹-R⁹ A²-R¹⁰ A³-R¹¹ X 1. —H —H —H 2 S C—Cl C—Cl —2. —H —H —H 2 C—CH₃ S C—CH₃ — 3. —H —H —H 2 C—CH₃ S C—H — 4. —H —H —H 1S C—CH₃ C—H — 5. —H —H —H 2 S C—CH₃ C—H — 6. —H —H —H 2 C—CH₃ S C—CH₃ —7. —H —H —H 2 O C—H C—H — 8. —H —H —H 2 C—H C—CH₃ S — 9. —H —H —H 2 SC—CH₃ C—H — 10. —H —H —H 2 S C—CH₃ C—H — 11. —H —H —H 2 S C—CH₃ C—H —12. —H —H —H 2 S C—CH₃ C—H — 13. —H —H —H 2 O C—H C—H — 14. —H —H —H 2 SC—CH₃ C—H — 15. —H —CH₃ —CH₃ 1 O C—CH₃ C—H CH₂ 16. —H —H —H 2 S C—CH₃C—H — 17. —H rac —H —H 1 S C—CH₃ C—H — 18. —H —H —H 1 C—H C—CH₃ S — 19.—H —H —H 2 C—H C—CH₃ S — 20. —H —H —H 2 S C—CH₃ C—CH₃ — 21. —H —CH₃ —CH₃1 O C—CH₃ C—H CH₂ 22. —H —H —H 2 S C—Cl C—H — 23. —H —H —H 2 S C—H C—H —24. —H —H —H 2 S C—H C—H — 25. —H —H —H 2 O C—CH₃ C—CH₃ — 26. —H —H —H 2S C—CH₃ C—H — 27. —H —H —H 2 S C—H C—H — 28. —H —H —H 2 O C—CH₃ C—H —29. —H —H —H 1 C—H C—H S — 30. —H —H —H 2 S C—CH₃ C—H — 31. —H —H —H 2 SC—CH₃ C—CH₃ — 32. —H —H —H 1 C—H C—H S — 33. —H —H —H 1 C—H C—H S — 34.—H —H —H 2 S C—C(CH₃)₃ C—H — 35. —H —H —H 2 S C—CH₃ C—H — 36. —H —H —H 2S C—H C—H — 37. —H —H —H 2 S C—H C—H — 38. —H —H —H 1 S C—CH₃ C—H — 39.—H —H —H 2 S C—CH₃ C—H — 40. —H —CH₃ —CH₃ 1 O C—CH₃ C—H CH₂ 41. —H —H —H2 S C—CF₃ C—H — 42. —H —H —H 2 S C—Cl C—H — 43. —H —H —H 2 S C—CH₃ C—H —44. —H —H —H 2 S C—CH₃ C—H — 45. —H S C—H C—H C(═O) 46. —H —H —H 2 S C—HC—H — 47. —H —H —H 2 S C—CH₃ C—H — 48. —H —H —H 1 C—H C—Cl S — 49. —H —H—H 1 C—H C—Cl S — 50. —H —H —H 1 C—H C—Cl S — 51. —CH₃ —H —H 2 S C—CH₃C—H — 52. —H —H —H 2 S C—CH₃ C—H — 53. —H —H —H 2 C—H C—Cl S — 54. —H —H—H 2 O C—H C—H — 55. —H —H —H 2 C—H C—CH₃ S — 56. —H —H —H 2 C—CH₃ SC—CH₃ — 57. —H —H —H 2 C—CH₃ S C—H — 58. —H —H —H 2 C—CH₃ C—CH₃ S — 59.—H —H —H 2 S C—CH₃ C—H — 60. —H —H —H 2 O C—H C—H — 61. —H —H —H 2 SC—CH₃ C—H — 62. —H —H —H 2 O C—CH₃ C—H — 63. —H —H —H 1 S C—CH₃ C—H —64. —H —H —H 2 C—CH₃ S C—CH₃ — 65. —H —H —H 2 C—H O C—H — 66. —H —H —H 2S C—H C—H — 67. —H —H —H 2 S C—CH₃ C—H — 68. —H —H —H 2 C—CH₃ S C—CH₃ —69. —H —H —H 2 C—H C—H S — 70. —H —H —H 2 S C—H C—H — 71. —H —H —H 2 SC—H C—H — 72. —H —H —H 2 S C—CH₃ C—H — 73. —H —H —H 2 S C—H C—H — 74. —H—H —H 2 S C—CH₃ C—H — 75. —H —H —H 2 S C—CH₃ C—H — 76. —H —H —H 2 SC—CH₃ C—H — 77. —H —H —H 1 S C—CH₃ C—H — 78. —H —H —H 2 S C—CH₂—CH₃ C—H— 79. —H —H —H 2 S C—CH₂—CH₃ C—H — 80. —H —H —H 2 S C—CH₃ C—H — 81. —H—H —H 2 C—H C—CH₃ S — 82. —H —H —H 2 S C—CH₃ C—H — 83. —H —H —H 2 SC—CH₃ C—H — 84. —H —H —H 2 C—CH₃ S C—CH₃ — 85. —H —H —H 2 S C—CH₃ C—H —86. —H —H —H 2 S C—CH₃ C—H — 87. —H —H —H 2 S C—CH₃ C—H — 88. —H —H —H 2S C—CH₃ C—H — 89. —H —H —H 2 S C—CH₃ C—H — 90. —H —H —H 2 S C—CH₃ C—H —91. —H —H —H 2 S C—CH₃ C—H — 92. —H —H —H 2 S C—CH₃ C—H — 93. —H —H —H 2S C—CH₃ C—H — 94. —H —H —H 2 S C—CH₃ C—H — 95. —H —H —H 2 S C—CH₃ C—H —96. —H —H —H 2 S C—CH₃ C—H — 97. —H —H —H 2 S C—CH₃ C—H — 98. —H —H —H 2S C—CH₃ C—H — 99. —H —H —H 2 S C—CH₃ C—H — 100. —H —H —H 2 S C—CH₃ C—H —101. —H —H —H 2 S C—CH₃ C—H — 102. —H —H —H 2 S C—CH₃ C—H — 103. —H —H—H 2 S C—CH₃ C—H — 104. —H —H —H 2 S C—CH₃ C—H — 105. —H —H —H 2 S C—CH₃C—H — 106. —H —H —H 2 S C—CH₃ C—H — 107. —H —H —H 2 S C—CH₃ C—H — 108.—H —H —H 2 S C—CH₃ C—H — 109. —H —H —H 2 S C—CH₃ C—H — 110. —H —H —H 2 SC—CH₃ C—H — 111. —H —H —H 2 S C—CH₃ C—H — 112. —H —H —H 2 S C—CH₃ C—H —113. —H —H —H 2 S C—CH₃ C—H — 114. —H —H —H 2 S C—H C—H — 115. —H —H —H2 S C—H C—H — 116. —H —H —H 2 S C—H C—H — 117. —H —H —H 2 S C—H C—H —118. —H —H —H 2 S C—H C—H — 119. —H —H —H 2 S C—H C—H — 120. —H —H —H 2S C—H C—H — 121. —H —H —H 2 S C—H C—H — 122. —H —H —H 2 S C—H C—H — 123.—H —H —H 2 S C—H C—H — 124. —H —H —H 2 S C—H C—H — 125. —H —H —H 2 S C—HC—H — 126. —H —H —H 2 S C—H C—H — 127. —H —H —H 2 S C—H C—H — 128. —H —H—H 2 S C—H C—H — 129. —H —H —H 2 S C—H C—H — 130. —H —H —H 2 S C—H C—H —131. —H —H —H 2 S C—H C—H — 132. —H —H —H 2 S C—H C—H — 133. —H —H —H 2S C—H C—H — 134. —H —H —H 2 S C—H C—H — 135. —H —H —H 2 S C—H C—H — 136.—H —H —H 2 S C—H C—H — 137. —H —H —H 2 S C—H C—H — 138. —H —H —H 2 SC—CH₃ C—H — 139. —H —H —H 2 S C—H C—H — 140. —H —H —H 2 S C—H C—H — 141.—H —H —H 2 S C—CH₃ C—H — 142. —H —H —H 2 S C—CH₃ C—H — 143. —H —H —H 2 SC—H C—H — 144. —H —H —H 2 S C—CH₃ C—H — 145. —H —H —H 2 S C—CH₃ C—H —146. —H —H —H 2 S C—CH₃ C—H — 147. —H —H —H 2 S C—CH₃ C—H — 148. —H —H—H 2 S C—CH₃ C—H — 149. —H —H —H 2 S C—CH₃ C—H — 150. —H —H —H 2 S C—CH₃C—H — 151. —H —H —H 2 S C—CH₃ C—H — 152. —H —H —H 2 S C—CH₃ C—H — 153.—H —H —H 2 S C—CH₃ C—H — 154. —H —H —H 2 S C—H C—H — 155. —H —H —H 2 SC—CH₃ C—CH₃ — 156. —H —H —H 2 S C—H C—H — 157. —H —H —H 2 S C—CH₃ C—H —158. —H —H —H 2 S C—H C—H — 159. —H —H —H 2 S C—H C—H — 160. —H —H —H 2S C—H C—H — 161. —H —H —H 2 S C—H C—H — 162. —H —H —H 2 S C—H C—H — 163.—H —H —H 2 S C—H C—H — 164. —H —H —H 2 S C—H C—H — 165. —H —H —H 2 S C—HC—H — 166. —H —H —H 2 S C—H C—H — 167. —H —H —H 2 S C—H C—H — 168. —H —H—H 2 S C—CH₃ C—H — 169. —H —H —H 2 S C—CH₃ C—H — 170. —H —H —H 2 S C—CH₃C—H — 171. —H —H —H 2 S C—H C—H — 172. —H —H —H 2 S C—CH₃ C—H — 173. —H—H —H 2 S C—CH₃ C—H — 174. —H —H —H 2 S C—CH₃ C—H — 175. —H —H —H 2 SC—CH₃ C—H — 176. —H —H —H 2 S C—H C—H — 177. —H —H —H 2 S C—CH₃ C—H —178. —H —H —H 2 S C—H C—H — 179. —H —H —H 2 O C—H C—H — 180. —H —H —H 2O C—H C—H — 181. —H —H —H 2 O C—H C—H — 182. —H —H —H 2 S C—CH₃ C—H —183. —H —H —H 2 S C—CH₃ C—H — 184. —H —H —H 2 S C—CH₃ C—H — 185. —H —H—H 2 S C—CH₃ C—H — 186. —H —H —H 2 S C—H C—H — 187. —H —H —H 2 S C—H C—H— 188. —H —H —H 2 S C—H C—H — 189. —H —H —H 2 S C—H C—H — 190. —H —H —H2 S C—H C—H — 191. —H —H —H 2 S C—H C—H — 192. —H —H —H 2 S C—H C—H —193. —H —H —H 1 S C—H C—H O 194. —H —H —H 1 S C—H C—H N—CH₃ 195. —H —H—H 1 S C—H C—H N—Ph 196. —H rac —H —H 2 S C—H C—H — 197. —H rac —H —H 2S C—H C—H — 198. —H —H 2 S C—H C—H — 199. —H —H —H 2 S C—CH₃ C—H — 200.—H —H —H 2 S C—H C—H — 201. —H —H —H 2 S C—H C—H — 202. —H —H —H 2 S C—HC—H — 203. —H —H —H 2 S C—H C—H — 204. —H —H —H 2 S C—H C—H — 205. —H R—H —H 2 S C—H C—H — 206. —H S —H —H 2 S C—H C—H — 207. —H —CH₃ —H 1 racS C—CH₃ C—H CH₂ 208. —H —Ph —H 1 rac S C—CH₃ C—H O 209. —H —CH₃ —H 1 R SC—CH₃ C—H CH₂ 210. —H —CH₃ —H 1 S S C—H C—H CH₂ 211. —H —H —H 2 S C—HC—H — 212. —H —H —H 2 S C—CH₃ C—H — 213. —H —H —H 2 S C—CH₃ C—CH₃ — 214.—H —H —H 2 S C—CH₃ C—CH₃ — 215. —H —H —H 1 S C—H C—H — 216. —H —H —H 2 SC—CH₂CH₃ C—H — 217. —H —H —H 1 C—H C—H S — 218. —H —H —H 2 C—H C—H S —219. —H —H —H 2 C—CH₃ S C—CH₃ — 220. —H —H —H 2 S C—CH₃ C—H — 221. —H —H—H 2 S C—CH₃ C—H — 222. —H —H —H 2 S C—CH₃ C—H — 223. —H —H —H 2 S C—HC—H — 224. —H —H —H 2 S C—CH₃ C—H — 225. —H —H —H 2 S C—H C—H — 226. —H—H —H 2 S C—CH₃ C—H — 227. —H —H —H 2 S C—H C—H — 228. —H —H —H 2 SC—CH₃ C—H — 229. —H —H —H 2 S C—H C—H — 230. —H —H —H 2 S C—H C—H — 231.—H —H —H 2 S C—H C—H — 232. —H —H —H 2 S C—CH₃ C—H — 233. —H —H —H 2 SC—CH₃ C—H — 234. —H —H —H 2 S C—CH₃ C—H — 235. —H —H —H 2 S C—H C—H —236. —H —H —H 2 S C—H C—H — 237. —H —H —H 2 S C—H C—H — 238. —H —H —H 2S C—H C—H — 239. —H —H —H 2 S C—CH₃ C—H — 240. —H —H —H 2 S C—CH₃ C—H —241. —H —H —H 2 S C—CH₃ C—H — 242. —H —H —H 2 S C—CH₃ C—H — 243. —H —H—H 2 S C—CH₃ C—H — 244. —H —H —H 2 S C—CH₃ C—H — 245. —H —H —H 2 S C—CH₃C—H — 246. —H —H —H 2 S C—H C—H — 247. —H rac —H —H 2 S C—H C—H — 248.—H 0 O C—H C—H —CO— 249. —H —H —H 1 O — 250. —H —H —H 2 C—H C—H O — 251.—H —H —H 2 C—H C—H O — 252. —H —H —H 2 C—H C—H O — 253. —H —H —H 2 C—HC—H O — 254. —H —H —H 2 C—H C—H O — 255. —H —H —H 2 C—H C—H O — 256. —H—H —H 1 S C—Cl C—H — 257. —H —H —H 2 S C—CH₃ C—H — 258. —H —H —H 2 SC—Cl C—H — 259. —H —H —H 2 S C—Cl C—H — 260. —H —H —H 2 S C—Cl C—H —261. —H —H —H 2 S C—Cl C—H — 262. —H —H —H 2 S C—Cl C—H — 263. —H —H —H2 S C—CH₃ C—H — 264. —H —H —H 2 S C—CH₃ C—H — 265. —H —H —H 2 S C—CH₃C—H — 266. —H —H —H 2 S C—CH₃ C—H — 267. —H —H —H 2 S C—CH₃ C—H — 268.—H —H —H 2 S C—CH₃ C—H — 269. —H —H —H 2 S C—CH₃ C—H — 270. —H —H —H 1 SC—H C—H — 271. —H —H —H 1 S C—H C—H — 272. —H —H —H 1 S C—CH₃ C—H — 273.—H —H —H 1 S C—CH₃ C—H — 274. —H —H —H 2 C—H C—CH₃ S — 275. —H —H —H 2 SC—CH₃ C—H — 276. —H —H —H 2 S C—Cl C—H — 277. —H —H —H 2 S C—Cl C—H —278. —H —H —H 2 S C—Cl C—H — 279. —H —H —H 2 S C—Cl C—H — 280. —H —H —H2 S C—CH₃ C—H — 281. —H —H —H 2 S C—CH₃ C—CH₃ — 282. —H —H —H 2 S C—CH₃C—H — 283. —H —H —H 2 S C—CH₃ C—H — 284. —H —H —H 2 S C—CH₃ C—H — 285.—H —H —H 2 C—H C—CN S — 286. —H —H —H 2 S C—CH₃ C—H — 287. —H —H —H 2 SC—CH₃ C—H — 288. —H —H —H 2 S C—CH₃ C—H — 289. —H —H —H 2 S C—CH₃ C—H —290. —H —H —H 2 S C—CH₃ C—H — 291. —H —H —H 2 S C—CH₃ C—H — 292. —H —H—H 2 S C—H C—H — 293. —H —H —H 2 S C—CH₃ C—H — 294. —H —H —H 2 S C—CH₃C—H — 295. —H —H —H 2 S C—CH₃ C—H — 296. —H —H —H 2 S C—CH₃ C—H — 297.—H —H —H 2 S C—CH₃ C—H — 298. —H —H —H 2 S C—CH₃ C—H — 299. —H —H —H 2 SC—CH₃ C—H — 300. —H —H —H 2 S C—CH₃ C—H — 301. —H —H —H 2 S C—H C—H —302. —H —H —H 2 S C—CH₃ C—H — 303. —H —H —H 2 S C—Cl C—H — 304. —H —H —H2 S C—CH₃ C—H — 305. —H —H —H 2 S C—CH₃ C—H — 306. —H —H —H 2 S C—CH₃C—H — 307. —H —H —H 2 S C—CH₃ C—H — 308. —H —H —H 2 S C—CH₃ C—H — 309.—H —H —H 2 S C—CH₃ C—H — 310. —H —H —H 2 S C—H C—H — 311. —H —H —H 2 SC—CH₃ C—H — 312. —H —H —H 2 S C—CH₃ C—H — 313. —H —H —H 2 S C—CH₃ C—H —314. —H —H —H 2 S C—CH₃ C—H — 315. —H —H —H 2 S C—CH₃ C—H — 316. —H —H—H 2 S C—CH₃ C—H — 317. —H —H —H 2 S C—CH₃ C—H — 318. —H —H —H 2 S C—CH₃C—H — 319. —H —H —H 2 S C—CH₃ C—H — 320. —H —H —H 2 S C—CH₃ C—H — 321.—H —H —H 2 S C—CH₃ C—H — 322. —H —H —H 2 S C—CH₃ C—H — 323. —H —H —H 2 SC—CH₃ C—H — 324. —H —H —H 2 S C—CH₃ C—H — 325. —H —H —H 2 S C—CH₃ C—H —326. —H —H —H 2 S C—H C—H — 327. —H —H —H 2 S C—CH₃ C—H — 328. —H —H —H2 S C—CH₃ C—H — 329. —H —H —H 2 S C—CH₃ C—H — 330. —H —H —H 2 S C—CH₃C—H — 331. —H —H —H 2 S C—CH₃ C—H — 332. —H —H —H 2 S C—CH₃ C—H — 333.—H —H —H 2 S C—CH₃ C—H — 334. —H —H —H 2 S C—CH₃ C—H — 335. —H —H —H 2 SC—CH₃ C—H — 336. —H —H —H 2 S C—CH₃ C—H — 337. —H —H —H 2 S C—CH₃ C—CH₃— 338. —H —H —H 2 S C—CH₃ C—CH₃ — 339. —H —H —H 2 S C—H C—H — 340. —H —H—H 2 S C—CH₃ C—H — 341. —H —H —H 2 S C—CH₃ C—H — 342. —H —H —H 2 S C—CH₃C—H — 343. —H —H —H 2 S C—CH₃ C—H — 344. —H —H —H 2 S C—CH₃ C—H — 345.—H —H —H 2 S C—CH₃ C—H — 346. —H —H —H 2 S C—CH₃ C—H — 347. —H —H —H 2 SC—CH₃ C—H — 348. —H —H —H 2 S C—CH₃ C—H — 349. —H —H —H 2 S C—Cl C—H —350. —H —H —H 2 S C—Cl C—H — 351. —H —H —H 2 S C—CH₃ C—H — 352. —H —H —H2 S C—CH₃ C—H — T1: 2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl T2:N2-5-(trifluoromethyl)pyrimidine-2,4-diamine T3:2-ethyl-4,5,6,7-tetrahydrobenzothiophen-4-yl T4:2-methyl-4,5,6,7-tetrahydrobenzothiophen-7-yl T5:(4R)-2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl T6:(E)-pyrrolidin-1-ylmethyleneamino T7: (E)-1-piperidylmethyleneamino T8:2,3-dimethyl-4,5,6,7-tetrahydrobenzothiophen-4-yl T9: cyclopentyl T10:2-chloro-4,5,6,7-tetrahydrobenzothiophen-7-yl T11:2-methyl-5,6-dihydro-4H-cyclopenta[b]thiophen-4-yl T12:5-(trifluoromethyl)pyrid-3-yl T13: 5-fluoropyrid-3-yl T14:5-chloropyrid-3-yl T15: 4-(2-pyridyl)piperazin-1-yl T16:4-(2-fluorophenyl)piperazin-1-yl T17: (1R,2S)-2,6-dimethylindan-1-ylT18: azepinyl T19: cyclopropyl

The present invention further provides processes for preparingcorresponding compounds of the general formula (I) and/or salts thereofand/or agrochemically acceptable quaternized nitrogen derivativesthereof:

-   a.) Compounds of the general formula (I)

-   -   in which the radicals R¹ to R¹¹, A¹ to A³, n and X have the        above meanings are prepared by reacting a compound of the        general formula (II)

-   -   in which R¹ to R³ have the above meaning and    -   W¹ represents an exchangeable radical or a leaving group, with        an amine of the general formula (III) or an acid addition salt        of the amine of the general formula (III)

-   -   where the radicals R⁴ to R¹¹, A¹ to A³, n and X have the above        meaning.    -   The exchangeable radical W¹ or the leaving group W¹ represents        fluorine, chlorine, bromine, iodine, a (C₁-C₄)-alkylsulfanyl or        a (C₁-C₄)-alkylsulfinyl or a (C₁-C₄)-alkylsulfonyl, an        unsubstituted or substituted phenyl-(C₁-C₄)-alkylsulfonyl or a        (C₁-C₄)-alkylphenylsulfonyl.    -   If necessary, a radical W¹ can be converted to another group of        better exchangeability. For example, in the context of a        two-stage one-pot method, (C₁-C₄)-alkylsulfanyl can be converted        with an oxidizing agent such as m-chloroperbenzoic acid or        Oxone® into (C₁-C₄)-alkylsulfinyl or (C₁-C₄)-alkylsulfonyl or        mixtures thereof, and then reacted with an amine of the general        formula (III) or an acid addition salt using an auxiliary base,        for example triethylamine or potassium carbonate.    -   The reaction may optionally also be catalyzed by various        auxiliaries, for example by the reagents potassium phosphate,        copper(I) iodide and N,N-diethyl-2-hydroxybenzamide, or in the        manner of a Buchwald-Hartwig coupling by special transition        metal catalyst systems.    -   The compounds of the general formula (II) are commercially        available or can be prepared by known methods.    -   The amines of the general formula (III) or the acid addition        salt thereof are commercially available, or the synthesis        thereof is described in DE 19921883.

-   b.) Compounds of the general formula (I) can also be prepared by    initially converting a compound of the general formula (III-a),

-   -   where at least one of the radicals R¹ to R³ represents a radical        Z¹ to Z³, where Z¹ to Z³ are selected from the group consisting        of COOH, COO(C₁-C₆)-alkyl, nitrile, C₂-C₆-alkynyl, halogen,        acetyl, carbonyl and (C₁-C₆)-alkylmercapto, which radical may be        modified or exchanged, analogously to the processes described        under a. with an amine of the formula (III) or an acid addition        salt thereof to give an intermediate of the formula (I-a)

-   -   and then, for example, converting the Z² radical to a ketone.        For example, in the case that Z²═(C₂-C₆)-alkynyl, the        (C₂-C₆)-alkynyl group can be converted to        —C(═O)—CH₂—(C₁-C₄)-alkynyl or, when Z²=trimethylsilylacetylene,        to ethynyl; for example, the Z² radical=COOH or COO(C₁-C₆)-alkyl        by methods known in the literature to C(═O)—R¹.    -   If necessary, a Z² radical can also be converted to another Z²        radical first. For example, by the methods described above, it        is thus possible first to prepare an intermediate of the (I-a)        type in which the Z² radical is a halogen and to convert the        halogen by methods known from the literature to a        (C₂-C₆)-alkynyl or a 1-(C₁-C₆)-alkoxy-(C₂-C₆)-alkenyl and then        to convert the Z² radical to a C(═O)—R¹.    -   If Z¹ to Z³ represent at least one ketone, this can be        converted, for example, with hydroxylamine or substituted        hydroxylamines or components released in situ from the        respective salt forms of the reagents to give the respective        target products.    -   If Z¹ to Z³ represent at least one halogen, preferably bromine        or iodine, this can be reacted for example under palladium        catalysis with alkenes or alkynes to give target structures        which, for example, carry (C₂-C₆)-alkynyls or (C₂-C₆)-alkenyls        as R¹ to R³.    -   In the case that Z¹ to Z³ is at least one nitrile, this can be        hydrolyzed, for example with bases such as aqueous sodium        hydroxide solution or potassium hydroxide to give carboxamides        R¹ to R³.    -   In the case that Z¹ to Z³ is at least one carboxylic ester, this        can be hydrolyzed, for example with bases such as aqueous sodium        hydroxide solution or potassium hydroxide to give carboxylic        acids R¹ to R³.    -   In the case that Z¹ to Z³ is at least one carboxylic acid, this        can be reacted, for example, with amines using auxiliary        reagents such as T3P, to give substituted carboxamides R¹ to R³.    -   In the case that Z¹ to Z³ is at least one carboxylic acid, this        can be converted into a carbonyl chloride and then be reacted        with amines to give substituted carboxamides R¹ to R³.    -   In the case that Z¹ and Z³ is at least one halogen atom, this        can be reacted, for example, with amines, optionally with the        use of additional bases such as triethylamine, to give amines at        position R¹ and R³.    -   In the case that Z¹ and Z³ is at least one halogen atom, this        can be reacted, for example, with alcohols, optionally with the        use of additional bases such as sodium, sodium hyhydride or the        alkoxide of the alcohol in question, to give alkoxy derivatives        at position R¹ and R³.    -   In the case that Z¹ and Z³ is at least one halogen atom, this        can be reacted, for example, with thiols, optionally with the        use of additional bases such as sodium, sodium hyhydride or the        thioxide of the thiol in question, to give alkylthio derivatives        at position R¹ and R³.    -   In the case that Z¹ to Z³ contains at least one sulfur atom,        this can be oxidized with oxidizing agents such as Oxone or        m-chloroperbenzoic acid.    -   In the case that Z¹ to Z³ is at least one halogen atom,        preferably bromine or iodine, this can be reacted for example        under palladium catalysis with phenyl- or heterocyclylboronic        acids to give phenyl or heterocyclyl derivatives in position R¹        to R³.

-   c.) Compounds of the general formula (I) can also be prepared by    condensing amidines of type (IV) or acid addition salts thereof

-   -   with a ketone of the formula (V)

-   -   in which the radical Z⁴ represents (C₁-C₆)-alkoxy or        di-(C₁-C₆)-alkylamino.

-   d.) Compounds of the general formula (I) can also be prepared in a    three-component reaction by condensing amidines of type (IV) or acid    addition salts

-   -   with a ketone of the formula (VI)

-   -   and with a fragment (VII) in which Z⁵ represents (C₁-C₆)-alkoxy        or di-(C₁-C₆)-alkylamino and Z⁶ represents (C₁-C₆)-alkoxy

-   e.) Compounds of the general formula (II) in which the radical W¹    represents (C₁-C₄)-alkylsulfanyl can be prepared analogously to the    methods described in c.) or d.), except using, rather than (IV),    S—(C₁-C₄)-alkylisothioureas or acid addition salts thereof.

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the abovementioned reactions can also be preparedin a parallelized manner, in which case this may be accomplished in amanual, partly automated or fully automated manner. It is possible, forexample, to automate the conduct of the reaction, the workup or thepurification of the products and/or intermediates. Overall, this isunderstood to mean a procedure as described, for example, by D. Tiebesin Combinatorial Chemistry—Synthesis, Analysis, Screening (editorGunther Jung), Wiley, 1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possibleto use a number of commercially available instruments, for examplereaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB113AZ, England, or MultiPROBE Automated Workstations from PerkinElmer,Waltham, Mass. 02451, USA. For the parallelized purification ofcompounds of the general formula (I) and salts thereof or ofintermediates which occur in the course of preparation, availableapparatuses include chromatography apparatuses, for example fromTeledyne ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which theindividual working steps are automated, but manual operations have to becarried out between the working steps. This can be circumvented by usingpartly or fully integrated automation systems in which the respectiveautomation modules are operated, for example, by robots.

The implementation of single or multiple synthesis steps can besupported by the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Aside from the methods described here, compounds of the general formula(I) and salts thereof can be prepared completely or partially bysolid-phase-supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid-phase-supported synthesis methods are described adequately in thetechnical literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis,Analysis, Screening (editor: Gunther Jung), Wiley, 1999. The use ofsolid-phase-supported synthesis methods permits a number of protocols,which are known from the literature and which for their part may beperformed manually or in an automated manner.

Both in the solid and in the liquid phase, the implementation ofindividual or several synthesis steps may be supported by the use ofmicrowave technology. The specialist literature describes a series ofexperimental protocols, for example in Microwaves in Organic andMedicinal Chemistry (editor: C. O. Kappe and A. Stadler), Wiley, 2005.

The preparation by the processes described here gives compounds of theformula (I) and salts thereof in the form of substance collections,which are called libraries. The present invention also provideslibraries comprising at least two compounds of the formula (I) and saltsthereof.

On account of the herbicidal property of the compounds of the generalformula (I), the invention also further provides for the use of thecompounds of the general formula (I) according to the invention asherbicides for control of harmful plants.

Herbicides are used in agriculturally utilized crops during variouscultivation phases. Thus, the application of some products even takesplace before or during sowing. Others are applied before the crop plantemerges, i.e. before the seedling breaks through the earth's surface

(pre-emergence herbicides). Finally, post-emergence herbicides are usedif either already the seed leaves or foliage leaves have been formed bythe crop plant.

The compounds of the invention can be employed either pre-emergence orpost-emergence, preference being given to pre-emergence use of thecompounds of the invention.

The pre-emergence treatment includes both the treatment of the areaunder cultivation prior to sowing (ppi=pre plant incorporation) and thetreatment of the sown areas of cultivation which do not yet sustain anygrowth.

The compounds of the formula (I) according to the invention and theirsalts, also referred to synonymously and collectively hereinafter ascompounds of the formula (I), have excellent herbicidal efficacy againsta broad spectrum of economically important monocotyledonous anddicotyledonous harmful plants. The active compounds also have goodcontrol over perennial weeds which are difficult to control and produceshoots from rhizomes, root stocks or other perennial organs. It does notmatter here whether the substances are applied by the presowing method,the pre-emergence method or the post-emergence method.

Specific examples of some representatives of the monocotyledonous anddicotyledonous weed flora which can be controlled by the compounds ofthe general formula (I) according to the invention are mentionedhereinafter, without any intention that the enumeration is to impose arestriction to particular species.

On the side of the monocotyledonous weed species, e.g. Agrostis,Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium,Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, Fimbristylis,Ischaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa,Sagittaria, Scirpus, Setaria, Sphenoclea, and also Cyperus speciespredominantly from the annual group and on the sides of the perennialspecies Agropyron, Cynodon, Imperata and Sorghum and also perennialCyperus species are well controlled.

In the case of dicotyledonous weed species, the spectrum of actionextends to species such as, for example,

Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis,Ipomoea, Matricaria, Abutilon and Sida on the annual side, andConvolvulus, Cirsium, Rumex and Artemisia in the case of the perennialweeds. Moreover, herbicidal action is observed in the case ofdicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea,Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga,Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa,Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium,Urtica and Xanthium.

If the compounds of the general formula (I) according to the inventionare applied to the soil surface before germination, either the emergenceof the weed seedlings is prevented completely or the weeds grow untilthey have reached the cotyledon stage, but then they stop growing andultimately die completely after three to four weeks have passed.

If the active compounds of the general formula (I) are appliedpost-emergence to the green parts of the plants, growth likewise stopsvery rapidly after the treatment, and the weed plants remain at thegrowth stage at the time of application or die completely after acertain time, such that competition by the weeds, which is harmful tothe crop plants, is thus eliminated very early and in a lasting manner.

Although the compounds of the general formula (I) according to theinvention have excellent herbicidal activity in respect ofmonocotyledonous and dicotyledonous weeds, crop plants of economicallyimportant crops, for example wheat, barley, rye, rice, corn, sugar beet,cotton, oilseed rape and soybean, are only damaged negligibly, if atall. This is why the present compounds are highly suitable for theselective control of unwanted plant growth in agriculturally usefulplants.

In addition, the substances of the general formula (I) according to theinvention have excellent growth regulatory properties in crop plants.They engage in the plant metabolism in a regulatory fashion and cantherefore be employed for the influencing, in a targeted manner, ofplant constituents and for facilitating harvesting, such as, forexample, by triggering desiccation and stunted growth. Furthermore, theyare also suitable for the general control and inhibition of unwantedvegetative growth without killing the plants in the process. Inhibitionof vegetative growth plays a major role for many mono- anddicotyledonous crops since this can, for example, reduce or completelyprevent lodging.

By virtue of their herbicidal and plant growth regulatory properties,the active compounds can also be used to control harmful plants in cropsof genetically modified plants which are known or are yet to bedeveloped. In general, the transgenic plants are characterized byparticular advantageous properties, for example by resistances tocertain pesticides, in particular certain herbicides, resistances toplant diseases or pathogens of plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with regard toquantity, quality, storability, composition and specific constituents.For instance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or those with a different fatty acidcomposition in the harvested material. Other particular properties maybe tolerance or resistance to abiotic stressors, for example heat, lowtemperatures, drought, salinity and ultraviolet radiation.

It is preferable to employ the compounds of the general formula (I)according to the invention or salts thereof in economically importanttransgenic crops of useful plants and ornamental plants, for example ofcereals such as wheat, barley, rye, oats, sorghum and millet, rice,cassava and corn or else crops of sugar beet, cotton, soybean, oilseedrape, potato, tomato, peas and other vegetables.

It is preferable to employ the compounds of the general formula (I) asherbicides in crops of useful plants which are resistant, or have beenmade resistant by recombinant means, to the phytotoxic effects of theherbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to existing plants consist, for example, intraditional cultivation methods and the generation of mutants.Alternatively, novel plants with altered properties can be generatedwith the aid of recombinant methods (see, for example, EP 0221044, EP0131624). For example, there have been descriptions in several cases of:

-   -   genetic modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (for example WO        92/011376, WO 92/014827, WO 91/019806),    -   transgenic crop plants which are resistant to certain herbicides        of the glufosinate type (cf., for example, EP 0242236,        EP 0242246) or the glyphosate type (WO 92/000377) or the        sulfonylurea type (EP 0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, which is capable of        producing Bacillus thuringiensis toxins (Bt toxins), which make        the plants resistant to certain pests (EP 0142924, EP 0193259),    -   transgenic crop plants having a modified fatty acid composition        (WO 91/013972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EP 0309862, EP        0464461),    -   genetically modified plants having reduced photorespiration,        which have higher yields and higher stress tolerance (EP        0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which feature higher yields or better        quality,    -   transgenic crop plants which feature a combination, for example,        of the abovementioned novel properties (“gene stacking”).

Numerous molecular biology techniques which can be used to produce noveltransgenic plants with modified properties are known in principle; see,for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer toPlants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg,or Christou, “Trends in Plant Science” 1 (1996) 423-431).

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or sequence alteration by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it ispossible, for example, to undertake base exchanges, remove parts ofsequences or add natural or synthetic sequences. To join the DNAfragments with one another, adapters or linkers can be placed onto thefragments, see e.g. Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd edition Cold Spring Harbor Laboratory Press, ColdSpring Harbor, N.Y., or Winnacker “Gene and Klone [Genes and clones]”,VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect, or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product.

To this end, it is firstly possible to use DNA molecules which encompassthe entire coding sequence of a gene product inclusive of any flankingsequences which may be present, and also DNA molecules which onlyencompass portions of the coding sequence, in which case it is necessaryfor these portions to be long enough to have an antisense effect in thecells. It is also possible to use DNA sequences which have a high degreeof homology to the coding sequences of a gene product, but are notcompletely identical to them.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to join the coding region to DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants may beplants of any desired plant species, i.e. not only monocotyledonous butalso dicotyledonous plants.

Thus, transgenic plants can be obtained whose properties are altered byoverexpression, suppression or inhibition of homologous (=natural) genesor gene sequences or expression of heterologous (=foreign) genes or genesequences.

It is preferable to use the compounds of the general formula (I)according to the invention in transgenic crops which are resistant togrowth regulators, for example, dicamba, or to herbicides which inhibitessential plant enzymes, for example acetolactate synthases (ALS), EPSPsynthases, glutamine synthases (GS) or hydroxyphenylpyruvatedioxygenases (HPPD), or against herbicides from the group of thesulfonylureas, glyphosate, glufosinate or benzoylisoxazoles andanalogous active compounds.

When the active compounds of the general formula (I) according to theinvention are employed in transgenic crops, not only do the effectstoward harmful plants observed in other crops occur, but frequently alsoeffects which are specific to application in the particular transgeniccrop, for example an altered or specifically widened spectrum of weedswhich can be controlled, altered application rates which can be used forthe application, preferably good combinability with the herbicides towhich the transgenic crop is resistant, and influencing of growth andyield of the transgenic crop plants.

The invention therefore also relates to the use of the compounds of thegeneral formula (I) according to the invention as herbicides for controlof harmful plants in transgenic crop plants.

The compounds of the general formula (I) can be formulated in variousways according to which biological and/or physicochemical parameters arerequired. Possible formulations include, for example: wettable powders(WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), dispersions based on oil or water, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), dressings, granules forscattering and soil application, granules (GR) in the form ofmicrogranules, spray granules, absorption and adsorption granules,water-dispersible granules (WG), water-soluble granules (SG), ULVformulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th. Ed. 1986,Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973, K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd.London.

The necessary formulation assistants, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964, Schonfeldt,“Grenzflächenaktive Äthylenoxidaddukte [Interface-active ethylene oxideadducts]”, Wiss. Verlagsgesell., Stuttgart 1976, Winnacker Küchler,“Chemische Technologie [Chemical Technology]”, Volume 7, C. HanserVerlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active compounds, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix.

Wettable powders are preparations which can be dispersed uniformly inwater and, as well as the active compound, apart from a diluent or inertsubstance, also comprise surfactants of the ionic and/or nonionic type(wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleylmethyltauride. Toproduce the wettable powders, the active herbicidal ingredients arefinely ground, for example in customary apparatuses such as hammermills, blower mills and air-jet mills, and simultaneously orsubsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents with addition of one ormore surfactants of the ionic and/or nonionic type (emulsifiers).Examples of emulsifiers which may be used are: calciumalkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionicemulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycolethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxidecondensation products, alkyl polyethers, sorbitan esters, for examplesorbitan fatty acid esters, or polyoxyethylene sorbitan esters, forexample polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active compound with finelydistributed solid substances, for example talc, natural clays, such askaolin, bentonite and pyrophillite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They can beproduced, for example, by wet grinding by means of standard commercialbead mills and optionally the addition of surfactants, as have alreadybeen listed above, for example, for the other types of formulation.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as

already listed above, for example, for the other formulation types.

Granules can be produced either by spraying the active compound ontoadsorptive granular inert material or by applying active compoundconcentrates to the surface of carriers, such as sand, kaolinites orgranular inert material, by means of adhesives, for example polyvinylalcohol, sodium polyacrylate or else mineral oils. Suitable activecompounds can also be granulated in the manner customary for theproduction of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan, fluidized-bed, extruder and spray granules,see e.g. processes in “Spray-Drying Handbook” 3rd Ed. 1979, G. GoodwinLtd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering1967, pages 147 if, “Perry's Chemical Engineer's Handbook”, 5th Ed.,McGraw Hill, New York 1973, p. 8-57.

For further details regarding the formulation of crop protection agents,see, for example, G. C. Klingman, “Weed Control as a Science”, JohnWiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S.A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally 0.1% to 99% by weight,especially 0.1% to 95% by weight, of active compound of the formula (I).

In wettable powders, the active compound concentration is, for example,about 10% to 90% by weight, the remainder to 100% by weight consistingof customary formulation components. In emulsifiable concentrates, theactive compound concentration may be about 1% to 90% and preferably 5%to 80% by weight. Formulations in the form of dusts comprise 1% to 30%by weight of active compound, preferably usually 5% to 20% by weight ofactive compound; sprayable solutions contain about 0.05% to 80% byweight, preferably 2% to 50% by weight of active compound. In the caseof water-dispersible granules, the active compound content dependspartially on whether the active compound is present in liquid or solidform and on which granulation auxiliaries, fillers, etc., are used. Inthe water-dispersible granules, the content of active compound is, forexample, between 1% and 95% by weight, preferably between 10% and 80% byweight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary stickers, wetters, dispersants,emulsifiers, penetrants, preservatives, antifreeze agents and solvents,fillers, carriers and dyes, defoamers, evaporation inhibitors and agentswhich influence the pH and the viscosity.

The compounds of the general formula (I) or salts thereof can be used assuch or in the form of their preparations (formulations) in acombination with other pesticidally active substances, for exampleinsecticides, acaricides, nematicides, herbicides, fungicides, safeners,fertilizers and/or growth regulators, for example in the form of afinished formulation or of a tank mix.

For application, the formulations in the commercial form are diluted ifappropriate in a customary manner, for example with water in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules. Dust-type preparations, granules for soilapplication or granules for scattering and sprayable solutions are notnormally diluted further with other inert substances prior toapplication.

The required application rate of the compounds of the general formula(I) varies according to the external conditions such as, inter alia,temperature, humidity and the type of herbicide used. It can vary withinwide limits, for example between 0.001 and 10.0 kg/ha or more of activesubstance, but it is preferably between 0.005 and 5 kg/ha.

The present invention is illustrated in more detail by the examplesbelow; however, these examples do not limit the invention in any way.

A. SYNTHESIS EXAMPLES5-Fluoro-N2-(2-methyl-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)pyrimidine-2,4-diamine(Ex.: 12)

0.15 g (1.01 mmol) of 2-chloro-5-fluoropyrimidine-4-amine, 0.249 g (1.22mmol) of (2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl)ammoniumchloride and 0.63 g (0.68 ml, 3.05 mol) of dicyclohexylethylamine in 2.0ml of 1-methyl-2-pyrrolidone are heated at 180° C. in a closed cuvettein the microwave for 90 minutes (Biotage Initiator,http://www.biotage.com/product-page/biotage-initiator). The crudemixture thus obtained is applied to silica gel and purified by columnchromatography with heptane/ethyl acetate as mobile phase. Concentrationgives 0.072 g of5-fluoro-N2-(2-methyl-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)pyrimidine-2,4-diamine(in waxy form) (22% yield at 85% purity).

5-(Trifluoromethyl)-N2-(2,6,6-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-4-yl)pyrimidine-2,4-diamine(Ex.: 21)

0.25 g of an about 1:1 mixture of2-chloro-5-(trifluoromethyl)pyrimidine-4-amine and4-chloro-5-(trifluoromethyl)pyrimidine-2-amine, 0.295 g (1.22 mmol) of2,6,6-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-4-amine and 0.53 g (0.58ml, 2.53 mol) of dicyclohexylethylamine in 2.0 ml of1-methyl-2-pyrrolidone are heated at 180° C. in a closed cuvette in themicrowave for 150 minutes (Biotage Initiator,http://www.biotage.com/product-page/biotage-initiator). The crudemixture thus obtained is applied to silica gel and separated andpurified by column chromatography with heptane/ethyl acetate as mobilephase. Concentration gives 0.326 g of5-(trifluoromethyl)-N2-(2,6,6-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-4-yl)pyrimidine-2,4-diamine(solid, 90% pure) and as second fraction5-(trifluoromethyl)-N4-(2,6,6-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-4-yl)pyrimidine-2,4-diamine(solid, melting point 182.6° C., 90% pure).

N2-(5,6-Dihydro-4H-cyclopenta[b]thiophen-6-yl)-5-methylsulfonylpyrimidine-2,4-diamine(Ex.: 33)

With stirring, 0.205 g (0.866 mmol) of 73% strengthmeta-chloroperbenzoic acid is added to a solution, cooled to 0-5° C., of0.10 g of 2-methylsulfanyl-5-methylsulfonylpyrimidine-4-amine (0.43mmol) in 3 ml of trichloromethane. The mixture is stirred for about 2hours, 0.32 g (0.45 ml, 3.03 mmol) of triethylamine is then added and0.08 g (0.46 mmol) of 5,6-dihydro-4H-cyclopenta[b]thiophen-6-ylammoniumchloride is subsequently added. With stirring, the reaction mixture isheated at gentle reflux for 180 min and allowed to stand overnight. Thecrude mixture thus obtained is applied to silica gel and separated andpurified by column chromatography with heptane/ethyl acetate as mobilephase. Concentration gives 0.087 g ofN2-(5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl)-5-methylsulfonylpyrimidine-2,4-diamine(solid, melting point 175.9° C., 62% yield at a purity of 95%).

5-Propylsulfonyl-N2-(4,5,6,7-tetrahydrobenzothiophen-4-yl)pyrimidine-2,4-diamine(Ex.: 37)

1.00 g (6.80 mmol) of 2-propylsulfonylacetonitrile and 0.97 g (1.08 ml,8.15 mmol) of N,N-dimethylformamide dimethyl acetal in 5 ml of methanolare stirred for two hours. The reaction mixture is then concentrated ona rotary evaporator. The solid obtained is taken up in a little heptaneand filtered off with suction. This gives 1.05 g of3-(dimethylamino)-2-propylsulfonylprop-2-enenitrile (solid, meltingpoint 123.6° C., yield 73% at a purity of 95%).

0.16 g (0.79 mmol) of3-(dimethylamino)-2-propylsulfonylprop-2-enenitrile, 0.20 g (0.86 mmol)of 1-(4,5,6,7-tetrahydro-1-benzothiophen-4-yl)guanidine and 0.214 g(0.218 ml, 1.18 mmol) of sodium methoxide as a 30% strength solution inmethanol in 5 ml of methanol are heated at reflux for one hour. Thereaction mixture is applied to silica gel and separated by columnchromatography with heptane/ethyl acetate as mobile phase. Concentrationgives 0.216 g of5-propylsulfonyl-N2-(4,5,6,7-tetrahydrobenzothiophen-4-yl)pyrimidine-2,4-diamine(solid, melting point 189.9° C.) (yield 74% at a purity of 95%).

5-Nitro-N2-(2,6,6-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-4-yl)pyrimidine-2,4-diamine(Ex.: 40)

0.15 g (0.85 mmol) of 2-chloro-5-nitropyrimidine-4-amine, 0.185 g (0.82mmol) of 2,6,6-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-4-amine and0.174 g (0.24 ml, 1.71 mol) of triethylamine in 1.5 ml ofN,N-dimethylacetamide are heated at 120° C. in a closed cuvette in themicrowave for 45 minutes (Biotage Initiator,http://www.biotage.com/product-page/biotage-initiator). The crudemixture thus obtained is applied to silica gel and purified by columnchromatography with heptane/ethyl acetate as mobile phase. Concentrationgives 0.095 g of5-nitro-N2-(2,6,6-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-4-yl)pyrimidine-2,4-diamine(solid) (28% yield at 85% purity).

N2-[(4R)-2-Methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine(Ex.: 47)

0.75 g (3.48 mmol) of 2,4-dichloro-5-(trifluoromethyl)pyrimidine areinitially charged in 10 ml of tetrahydrofuran and cooled to 0° C., 1.036g of zinc chloride (10.86 ml of a 0.7 mol solution in tetrahydrofuran,7.60 mol) are then added dropwise and the mixture is stirred for onehour. Subsequently, 0.81 g (3.97 mmol) of[(4R)-2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl]ammonium chloride isadded and 0.84 g (1.156 ml, 8.27 mmol) of triethylamine is then addeddropwise. The reaction mixture is stirred for two hours and allowed towarm to room temperature. The reaction mixture is allowed to standovernight and then applied to silica gel. The reaction mixture, appliedto silica gel, is added to a frit covered with silica gel (height of thelayer about 1 cm) and the crude product is eluted using ethyl acetate.Concentration of the organic phase gives 1.23 g of4-chloro-N-[(4R)-2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl]-5-(trifluoromethyl)pyrimidine-2-amine(about 70%). This mixture is used for the next step without furtherpurification.

1.23 g of a mixture of4-chloro-N-[(4R)-2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl]-5-(trifluoromethyl)pyrimidine-2-amine(about 70%) and2-chloro-N-[(4R)-2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl]-5-(trifluoromethyl)pyrimidine-4-amine(about 20%) are heated in 3.5 ml of ammonia in methanol (about 12%strength solution, about 3.6 mmol) at 110° C. in a closed cuvette in themicrowave for 90 minutes (Biotage Initiator,http://www.biotage.com/product-page/biotage-initiator). <After heating,the pressure in the vial, indicated at the instrument, was about 8 bar).After cooling and venting, the crude mixture thus obtained is applied tosilica gel and separated and purified by column chromatography withheptane/ethyl acetate as mobile phase. Concentration gives 0.721 g ofN2-[(4R)-2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine(purity 95%) and as second fractionN4-[(4R)-2-methyl-4,5,6,7-tetrahydrobenzothiophen-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine(purity 95%).

N-(1,3-Dimethyl-4,5,6,7-tetrahydro-2-benzothiophen-4-yl)-5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine-2-amine(Ex.: 68)

2.5 g (16.8 mmol) of 1,1-dioxothian-3-one and 2.0 g (16.8 mmol) ofN,N-dimethylformamide dimethyl acetal are initially charged in 7 ml ofN,N-dimethylacetamide and stirred for 30 minutes, 2.59 g (9.27 mmol) of2-methyl-2-thiopseudourea sulfate and 1.88 g (2.59 ml, 18.5 mmol) oftriethylamine are added and the mixture is heated at 160° C. in a closedcuvette in the microwave for 40 minutes (Biotage Initiator,http://www.biotage.com/product-page/biotage-initiator). The crudemixture thus obtained is applied to silica gel and purified by columnchromatography with heptane/ethyl acetate as mobile phase. Concentrationgives 2.04 g of2-methylsulfanyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine 5,5-dioxide(solid) (yield 51% at a purity of 95%).

With stirring, 0.293 g (1.24 mmol) of 73% strength meta-chloroperbenzoicacid is added to a solution, cooled to 0-5° C., of 0.15 g of2-methylsulfanyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine 5,5-dioxide(0.62 mmol) in 5 ml of trichloromethane. The mixture is stirred forabout 2 hours, 0.33 g (0.45 ml, 3.10 mmol) of triethylamine is thenadded and 0.13 g (0.71 mmol) of1,3-dimethyl-4,5,6,7-tetrahydro-2-benzothiophene-4-amine is subsequentlyadded. With stirring, the reaction mixture is heated at gentle refluxfor 180 min and allowed to stand overnight. The crude mixture thusobtained is applied to silica gel and separated and purified by columnchromatography with heptane/ethyl acetate as mobile phase. Concentrationgives 0.044 g ofN-(1,3-dimethyl-4,5,6,7-tetrahydro-2-benzothiophen-4-yl)-5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine-2-amine(solid; 19% at a purity of 95%).

N2-(2,3-Dimethyl-4,5,6,7-tetrahydrobenzothiophen-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine(Ex.: 213)

0.40 g (1.84 mmol) of 2,4-dichloro-5-(trifluoromethyl)pyrimidine areinitially charged in 10 ml of tetrahydrofuran and cooled to 0° C., 0.55g of zinc chloride (5.80 ml of a 0.7 mol solution in tetrahydrofuran,4.07 mol) are then added dropwise and the mixture is stirred for onehour. Subsequently, 0.44 g (2.03 mmol) of(2,3-dimethyl-4,5,6,7-tetrahydrobenzothiophen-4-yl)ammonium chloride isadded and 0.45 g (0.62 ml, 4.42 mmol) of triethylamine is then addeddropwise. The reaction mixture is stirred for two hours and allowed towarm to room temperature. The reaction mixture is allowed to standovernight and then applied to silica gel. The reaction mixture, appliedto silica gel, is added to a frit covered with silica gel (height of thelayer about 1 cm) and the crude product is eluted using ethyl acetate.After concentration of the organic phase the crude mixture istransferred into a microwaveable vial and 5 ml of ammonia in methanol(about 12% strength solution, about 6 mmol) are added. In a closedcuvette, the mixture is heated in the microwave (Biotage Initiator,http://www.biotage.com/product-page/biotage-initiator) at 110° C. for 90minutes. <After heating, the pressure in the vial, indicated at theinstrument, was about 9 bar). After cooling and venting, the crudemixture thus obtained is applied to silica gel and separated andpurified by column chromatography with heptane/ethyl acetate as mobilephase. Concentration gives 0.261 g ofN2-(2,3-dimethyl-4,5,6,7-tetrahydrobenzothiophen-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine(solid, melting point 190.7° C., purity 95%) and as second fraction0.078 g ofN4-(2,3-dimethyl-4,5,6,7-tetrahydrobenzothiophen-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine(solid, purity 95%).

Table 2 (physicochemical characterization of selected synthesisexamples)

TABLE 2 Compound Description 2 solid, m.p.: 198.7° C.; logP (HCOOH):2.53; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.75 (m, 3H, 3H of CH₂); 2.05(m, 1H, 1H of CH₂); 2.25 (s, 6H, 2*3H of thiophene- CH₃); 2.45 (m, 1H,1H of CH₂); 2.65 (m, 1H, 1H of CH₂); 4.90 (m, 1H, 1H of CH); 5.15 (br,2H, NH₂); 5.75 (br, 1H, 1H of NH); 7.90 and 8.25 (2*br, 1H, Pyr-6H); 4solid; m.p.: 190.9° C.; logP (HCOOH): 1.73; 1H NMR (CDCl₃, 400 MHZ, δ inppm): 2.20 (m, 1H, 1H of CH₂); 2.45 (s, 3H, 3H of thiophene-CH₃);2.80-3.00 (m, 3H, 3H of CH₂); 3.05 (s, 3H, 3H of SO₂—CH₃); 5.30 (m, 1H,1H of CH); 5.50 (br, 2H, NH₂); 5.90 (br, 1H, 1H of NH); 6.55 (s, 1H,thiophene-H); 8.25 and 8.50 (2*br, 1H, Pyr-6H); 5 solid; logP (HCOOH):5.72; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 6H, 6H of CH₂); 2.10(m, 2H, 2H of CH₂); 2.40 (s, 6H, 2*3H of thiophene-CH₃); 2.60-2.80 (m,4H, 4H of CH₂); 5.00-5.40 (m, 3H, 2H of CH, 1H of NH); 6.50 (br, 1H, 1Hof NH); 6.50 (s, 1H, thiophene-H); 7.95 and 8.20 (2*br, 1H, Pyr-6H); 6solid; m.p.: 212.4° C.; logP (HCOOH): 2.44; 1H NMR (CDCl₃, 400 MHZ, δ inppm): 1.75 (m, 3H, 3H of CH₂); 2.05 (m, 1H, 1H of CH₂); 2.25 (s, 6H,2*3H of thiophene- CH₃); 2.40 (m, 1H, 1H of CH₂); 2.65 (m, 1H, 1H ofCH₂); 3.05 (s, 3H, 3H of SO₂—CH₃); 5.10 (m, 1H, 1H of CH); 5.15 (br, 2H,2H of NH₂); 5.75 (br, 1H, 1H of NH); 8.20 and 8.50 (2*br, 1H, Pyr-6H); 7oily 8 oily; logP (HCOOH): 3.19; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85(m, 3H, 3H of CH₂); 2.05 (m, 3H, 3H of CH₂); 2.40 (s, 3H, 3H of CH₃);2.60 (m, 4H, 4H of CH₂); 2.80 (m, 1H, 1H of CH₂); 2.90 (m, 1H, 1H ofCH₂); 5.40 (m, 1H, 1H of CH); 5.85 (br, 1H, 1H of NH); 6.45 (s, 1H,thiophene-H); ); 8.80 and 8.95 (2*br, 1H, Pyr-6H); 9 oily; logP (HCOOH):3.23; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3H of CH₂); 2.10(m, 3H, 3H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.60 (m, 2H, 2H of CH₂);2.75 (m, 3H, 3H of CH₂); 2.90 (m, 1H, 1H of CH₂); 5.25 (m, 1H, 1H ofCH); 5.85 (br, 1H, 1H of NH); 6.50 (s, 1H, thiophene-H); ); 8.80 and8.95 (2*br, 1H, Pyr-6H); 10 oily; logP (HCOOH): 4.76; 1H NMR (CDCl₃, 400MHZ, δ in ppm): 1.85 (m, 3H, 3H of CH₂); 2.10 (m, 1H, 1H of CH₂); 2.40(s, 3H, 3H of thiophene-CH₃); 2.60-2.80 (m, 2H, 2H of CH₂); 3.90 and4.00 (2*br, 3H, OCH₃); 5.00-5.40 (m, 1H, 1H of CH); 6.00 (br, 1H, 1H ofNH); 6.50 (s, 1H, thiophene-H); 8.05 and 8.30 (2*br, 1H, Pyr-6H); 11solid; m.p.: 134.4° C.; logP (HCOOH): 2.20; 1H NMR (CDCl₃, 400 MHZ, δ inppm): 1.85 (m, 3H, 3H of CH₂); 2.10 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3Hof thiophene- CH₃); 2.60-2.80 (m, 2H, 2H of CH₂); 4.80-5.50 (m, 4H, 1Hof CH, 1H of NH; 2H of NH₂); 6.50 (s, 1H, thiophene-H); 8.05 and 8.20(2*br, 1H, Pyr-6H); 12 oily; logP (HCOOH): 1.07; 1H NMR (CDCl₃, 400 MHZ,δ in ppm): 1.85 (m, 3H, 3H of CH₂); 2.10 (m, 1H, 1H of CH₂); 2.40 (s,3H, 3H of thiophene-CH₃); 2.60-2.80 (m, 2H, 2H of CH₂); 4.80-5.50 (br,4H, 1H of CH, 1H of NH; 2H of NH₂); 6.50 (s, 1H, thiophene-H); 7.80 and8.00 (2*br, 1H, Pyr-6H); 13 solid; m.p.: 222.1° C.; logP (HCOOH): 1.53;1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.80 (m, 1H, 1H of CH₂); 1.90 (m, 2H,2H of CH₂); 2.05 (m, 1H, 1H of CH₂); 2.60 (m, 2H, 2H of CH₂); 3.05 (s,3H, 3H of SO₂—CH₃); 5.00, 5.15, 5.40, 5.65 (each br, 4H, 1H of CH, 1H ofNH, 2H, NH₂); 6.30 (s, 1H, furan-H); 8.30 and 8.50 (2*br, 1H, Pyr-6H);15 oily; logP (HCOOH): 2.36; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.05 (s,3H, 3H of CH₃); 1.10 (s, 3H, 3H of CH₃); 1.35 (m, 1H, 1H of CH₂); 1.95(m, 1H, 1H of CH₂); 2.20 (s, 3H, 3H of furan-CH₃); 2.40 (dd, 2H, 2H ofCH₂); 3.00 (s, 3H, 3H of SO₂—CH₃); 5.00, 5.15, 5.20, 5.45 (each br, 4H,1H of CH, 1H of NH, 2H, NH₂); 5.90 (s, 1H, furan-H); 8.30 and 8.50(2*br, 1H, Pyr-6H); 16 oily; logP (HCOOH): 3.12; 1H NMR (CDCl₃, 400 MHZ,δ in ppm): 1.75 (m, 1H, 1H of CH₂); 1.85 (m, 2H, 2H of CH₂); 2.05 (m,1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.75 (m, 2H, 2H of CH₂); 3.30(s, 3H, 3H of SO₂CH₃); 5.00 to 5.60 and 7.80-8.10 (each br, 4H, 1H ofCH, 1H of NH; 2H of NH_(2;) 1H); 6.50 (s, 1H, thiophene-H); 17 oily;logP (HCOOH): 2.11; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.30 (d, 3H, 3Hof CH₃); 2.40 (s, 3H, 3H of thiophene-CH₃); 2.45 (m, 1H, 1H of CH₂);2.60 (m, 1H, 1H of CH₂); 3.05 (s, 3H, 3H of SO₂—CH₃); 3.15 (m, 1H, 1H ofCH₂); 4.90, 5.05, 5.50, 5.85 (each br, 4H, 1H of CH, 1H of NH, 2H, NH₂);6.50 (s, 1H, thiophene-H); 8.25 and 8.45 (2*br, 1H, Pyr-6H); 19 oily;logP (HCOOH): 2.21; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 1Hof CH₂); 2.10 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of thiophene-CH₃);2.55 (m, 2H, 2H of CH₂); 3.05 (s, 3H, 3H of SO₂—CH₃); 5.15, 5.30, 5.70,6.05 (each br, 4H, 1H of CH, 1H of NH, 2H, NH₂); 6.40 (s, 1H,thiophene-H); 8.25 and 8.45 (2*br, 1H, Pyr-6H); 21 solid; logP (HCOOH):2.23; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.05 (s, 3H, 3H of CH₃); 1.10(s, 3H, 3H of CH₃); 1.35 (m, 1H, 1H of CH₂); 1.95 (m, 1H, 1H of CH₂);2.20 (s, 3H, 3H of furan-CH₃); 2.35 (dd, 2H, 2H of CH₂); 3.00 (s, 3H, 3Hof SO₂—CH₃); 4.9-5.30 (br, 4H, 1H of CH, 1H of NH, 2H, NH₂); 5.85 (s,1H, furan-H); 8.05- 8.25 (br, 1H, Pyr-6H); 22 oily; logP (HCOOH): 1.07;1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.75 (m, 1H, 1H of CH₂); 1.85 (m, 2H,2H of CH₂); 2.10 (m, 1H, 1H of CH₂); 2.65 (m, 2H, 2H of CH₂); 5.05 and5.60 (br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.70 (s, 1H, thiophene-H);8.00-8.25 (br, 1H, Pyr-6H); 23 solid; m.p.: 196.2° C.; logP (HCOOH):1.82; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3H of CH₂); 2.10(m, 1H, 1H of CH₂); 2.85 (m, 2H, 2H of CH₂); 3.00 (s, 3H, 3H ofSO₂—CH₃); 5.15, 5.30, 5.50, 5.85 (each br, 4H, 1H of CH, 1H of NH; 2H ofNH₂); 6.85 (d, 1H, thiophene-H); 7.05 (d, 1H, thiophene-H); 8.25 and8.50 (br, 1H, Pyr-6H); 24 solid; logP (HCOOH): 1.82; 1H NMR (CDCl₃, 400MHZ, δ in ppm): 1.85 (m, 3H, 3H of CH₂); 2.10 (m, 1H, 1H of CH₂); 2.85(m, 2H, 2H of CH₂); 3.00 (s, 3H, 3H of SO₂—CH₃); 5.15, 5.30, 5.50, 5.65(each br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.85 (d, 1H, thiophene-H);7.05 (d, 1H, thiophene-H); 8.30 and 8.50 (br, 1H, Pyr-6H); 27 oily; logP(HCOOH): 1.95; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3H ofCH₂); 2.10 (m, 1H, 1H of CH₂); 2.85 (m, 2H, 2H of CH₂); 3.10 (s, 1H, 1Hof SO—NH); 5.15, 5.30, 5.50, 5.65 (each br, 4H, 1H of CH, 1H of NH; 2Hof NH₂); 6.85 (d, 1H, thiophene-H); 7.05 (d, 1H, thiophene-H); 7.50 (m,3H, 3H of Ar—H); 8.00 (m, 2H, 2H of Ar—H); 8.40 and 8.60 (br, 1H,Pyr-6H); 28 oily 29 oily; logP (HCOOH): 1.73; 1H NMR (CDCl₃, 400 MHZ, δin ppm): 2.20 (m, 1H, 1H of CH₂); 2.70 (m, 1H, 1H of CH₂); 2.85-3.05 (m,2H, 2H of CH₂); 4.90-5.70 (2*br, 4H, 1H of CH; 1H of NH; 2H of NH₂); 6.8(d, 1H, thiophene-H); 8.15 (br, 1H, Pyr- 6H); 30 oily; logP (HCOOH):4.27; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3H of CH₂); 2.05(m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.75 (m, 2H, 2H of CH₂);5.00 to 5.60 and 7.80 to 8.10 (each br, 4H, 1H of CH, 1H of NH; 2H ofNH_(2;) 1H); 6.55 (s, 1H, thiophene-H); 8.70 and 8.90 (2*br, 1H,Pyr-6H); 32 solid; m.p.: 189.5° C.; logP (HCOOH): 1.53; 33 solid; m.p.:175.9° C.; logP (HCOOH): 1.57; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 2.30(m, 1H, 1H of CH₂); 2.70 (m, 1H, 1H of CH₂); 2.85-3.00 (m, 2H, 2H ofCH₂); 3.05 (s, 3H, 3H of SO₂—CH₃); 5.40-5.85 (each br, 4H, 1H of CH, 1Hof NH; 2H of NH₂); 6.70 (d, 1H, thiophene-H); 7.25 (d, 1H, thiophene-H);8.30 and 8.50 (2*br, 1H, Pyr-6H); 35 oily; logP (HCOOH): 3.44; 1H NMR(CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3H of CH₂); 2.05 (m, 1H, 1H ofCH₂); 2.40 (s, 3H, 3H of CH₃); 2.75 (m, 2H, 2H of CH₂); 2.95 (s, 3H, 3Hof SOCH₃); 5.00 to 5.60 and 7.80-8.10 (each br, 4H, 1H of CH, 1H of NH;2H of NH_(2;) 1H); 6.55 (s, 1H, thiophene-H); 36 solid; m.p.: 243.3° C.;logP (HCOOH): 2.12; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.00 (m, 2H, 2Hof cyclopropyl); 1.25 (m, 2H, 2H of cyclopropyl); 1.85 (m, 3H, 3H ofCH₂); 2.10 (m, 1H, 1H of CH₂); 2.55 (m, 1H, 1H of cyclopropyl); 2.85 (m,2H, 2H of CH₂); 5.15, 5.30, 5.50, 5.65 (each br, 4H, 1H of CH, 1H of NH;2H of NH₂); 6.90 (d, 1H, thiophene-H); 7.05 (d, 1H, thiophene-H); 8.20and 8.40 (br, 1H, Pyr-6H); 37 solid; m.p.: 189.9° C.; logP (HCOOH):2.33; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.00 (t, 3H, 3H of CH₃);1.70-1.95 (m, 5H, 3H of CH₂, 2H of CH₂); 2.10 (m, 1H, 1H of CH₂); 2.85(m, 2H, 2H of CH₂); 3.05 (m, 2H, 2H of CH₂); 5.15, 5.20, 5.50, 5.85(each br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.85 (d, 1H, thiophene-H);7.05 (d, 1H, thiophene-H); 8.20 and 8.40 (br, 1H, Pyr-6H); 38 oily; logP(HCOOH): 2.54; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 2.20 (m, 1H, 1H ofCH₂); 2.45 (s, 3H, 3H of CH₃); 2.70-3.00 (m, 3H, 3H of CH₂); 4.10 (m,2H, 2H of CH₂—Ph); 4.85 (m, 1H, 1H of CH) 5.20-5.85 (each br, 4H, 1H ofNH; 1H of NH; 2H of NH₂); 6.55 (s, 1H, thiophene-H); 7.00 and 7.25(eachm, each 2 H, each 2 H of Ph); 8.20 and 8.45 (2*br, 1H, Pyr-6H); 39 oily;logP (HCOOH): 3.00; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.75 (m, 1H, 1Hof CH₂); 1.85 (m, 2H, 2H of CH₂); 2.05 (m, 1H, 1H of CH₂); 2.40 (s, 3H,3H of CH₃); 2.75 (m, 2H, 2H of CH₂); 2.90 (s, 3H, 3H of SOCH₃); 5.00 to5.60 and 7.80-8.10 (each br, 4H, 1H of CH, 1H of NH; 2H of NH_(2;) 1H);6.50 (s, 1H, thiophene-H); 40 solid; logP (HCOOH): 3.20; 42 oily; logP(HCOOH): 2.33; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.80 (m, 1H, 1H ofCH₂); 1.90 (m, 2H, 2H of CH₂); 2.10 (m, 1H, 1H of CH₂); 2.65 (m, 2H, 2Hof CH₂); 3.05 (s, 3H, 3H of SO₂—CH₃); 5.05, 5.15, 5.40 and 5.70 (eachbr, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.70 (s, 1H, thiophene-H); 8.30and 8.45 (2*br, 1H, Pyr-6H); 44 oily; logP (HCOOH): 2.94; 1H NMR (CDCl₃,400 MHZ, δ in ppm): 1.80 (m, 1H, 1H of CH₂); 1.90 (m, 2H, 2H of CH₂);2.10 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.45 (m, 2H, 2H ofCH₂); 2.65-2.95 (m, 3H, 2*2H of CH₂); 3.30 (m, 2H, 2H of CH₂); 5.15 (br,1H, 1H of NH); 5.70 and 5.90 (br, 1H, 1H of CH); 6.50 (s, 1H, thiophene-H); 8.65 and 8.80 (2*br, 1H, Pyr-6H); 45 solid; m.p.: 250.9° C.; logP(HCOOH): 0.91; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 2.85 (m, 1H, 1H ofCH₂); 3.05 (m, 2H, 2H of CH₂); 3.50 (m, 1H, 1H of CH₂); 5.40 to 6.05(each br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 7.15 (d, 1H, thiophene-H);7.95 (d, 1H, thiophene-H); 8.35 and 8.45 (br, 1H, Pyr-6H); 46 oily; logP(HCOOH): 1.91; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.80-1.95 (m, 3H, 3Hof CH₂); 2.10 (m, 1H, 1H of CH₂); 2.85 (m, 2H, 2H of CH₂); 4.90 to 5.70(each br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.90 (d, 1H, thiophene-H);7.05 (d, 1H, thiophene-H); 8.00 and 8.20 (br, 1H, Pyr-6H); 47 oily; logP(HCOOH): 2.62; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.80-1.95 (m, 3H, 3Hof CH₂); 2.10 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.70 (m, 2H,2H of CH₂); 4.90 to 5.90 (each br, 4H, 1H of CH, 1H of NH; 2H of NH₂);6.55 (s, 1H, thiophene-H); 7.90 and 8.20 (br, 1H, Pyr-6H); 48 oily; logP(HCOOH): 2.57; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 2.10 (m, 1H, 1H ofCH₂); 2.70 (m, 1H, 1H of CH₂); 2.85 (m, 2H, 2H of CH₂); 5.00 to 5.90(each br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.65 (s, 1H, thiophene-H);8.15 (br, 1H, Pyr-6H); 49 solid; logP (HCOOH): 2.32; 50 oily; logP(HCOOH): 2.15; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 2.10 (m, 1H, 1H ofCH₂); 2.70 (m, 1H, 1H of CH₂); 2.85 (m, 2H, 2H of CH₂); 3.05 (s, 3H, 3Hof SO₂—CH₃); 5.25 to 6.10 (each br, 4H, 1H of CH, 1H of NH; 2H of NH₂);6.65 (s, 1H, thiophene-H); 8.25 and 8.50 (br, 1H, Pyr-6H); 52 solid;m.p.: 178.0° C.; logP (HCOOH): 2.36; 1H NMR (DMSO, 400 MHZ, δ in ppm):1.70 (m, 2H, 2H of CH₂); 1.85-2.00 (m, 2H, 2H of CH₂); 2.30 (s, 3H, 3Hof CH₃); 2.65 (m, 2H, 2H of CH₂); 5.00 (br, 1H, 1H of CH); 6.45 (2s, 1H,thiophene-H); 7.00 and 7.20 (2br, 2H, 2H of NH₂); 7.50 and 7.70 (2d, 1Hof NH; 1H of NH); 8.15 and 8.30 (br, 1H, Pyr-6H); 53 solid; logP(HCOOH): 2.41; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.75-2.00 (m, 3H, 3Hof CH₂); 2.10 (m, 1H, 1H of CH₂); 2.65 (m, 2H, 2H of CH₂); 3.05 (s, 3H,3H of SO₂—CH₃); 5.15 to 5.75 (each br, 4H, 1H of CH, 1H of NH; 2H ofNH₂); 6.60 (s, 1H, thiophene-H); 8.30 and 8.50 (br, 1H, Pyr-6H); 54oily; logP (HCOOH): 2.35; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.80-2.00(m, 4H, 2*2H of CH₂); 2.10 (m, 4H, 2*2H of CH₂); 2.70 (m, 4H, 2*2H ofCH₂); 2.75 and 2.85 (2*m, 2H, 2H of CH₂); 5.20 (br, 1H, 1H of CH); 5.80(br, 1H, 1H of CH); 6.30 (s, 1H, furan-H); 8.80 and 8.95 (br, 1H,Pyr-6H); 55 oily; logP (HCOOH): 2.46; 1H NMR (CDCl₃, 400 MHZ, δ in ppm):1.85-2.00 (m, 3H, 3H of CH₂); 2.10 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3Hof CH₃); 2.60 (m, 2H, 2H of CH₂); 4.90 to 5.75 (each br, 4H, 1H of CH,1H of NH; 2H of NH₂); 6.45 (s, 1H, thiophene-H); 7.00 and 7.20 (2br, 2H,2H of NH₂); 8.00 and 8.20 (br, 1H, Pyr-6H); 56 oily; logP (HCOOH): 2.66;59 solid; m.p.: 215.3° C.; logP (HCOOH): 2.21; 1H NMR (DMSO, 400 MHZ, δin ppm): 1.85-2.00 (m, 3H, 3H of CH₂); 2.05 (m, 1H, 1H of CH₂); 2.35 (s,3H, 3H of CH₃); 2.70 (m, 2H, 2H of CH₂); 3.05 (s, 3H, 3H of SO₂—CH₃);5.05, 5.15, 5.45 and 5.70 (each br, 4H, 1H of CH, 1H of NH; 2H of NH₂);6.50 (s, 1H, thiophene-H); 8.30 and 8.50 (br, 1H, Pyr-6H); 60 solid;m.p.: 218.2° C.; logP (HCOOH): 2.57; 1H NMR (CDCl₃, 400 MHZ, δ in ppm):1.85-2.10 (m, 4H, 4H of CH₂); 2.50 (s, 3H, 3H of CH₃); 2.60 (m, 2H, 2Hof CH₂); 3.05 (s, 3H, 3H of SO₂—CH₃); 5.20 and 5.80 (each br, 2H, 1H ofCH, 1H of NH); 6.30 (s, 1H, furan-H); 8.60 and 8.80 (br, 1H, Pyr-6H); 61solid; m.p.: 169.1° C.; 62 oily; logP (HCOOH): 1.78; 1H NMR (CDCl₃, 400MHZ, δ in ppm): 1.70-2.00 (m, 4H, 4H of CH₂); 2.20 (s, 3H, 3H of CH₃);2.55 (m, 2H, 2H of CH₂); 4.90 to 5.75 (each br, 4H, 1H of CH, 1H of NH;2H of NH₂); 5.90 (s, 1H, furan-H); 8.30 and 8.50 (br, 1H, Pyr-6H); 63solid; logP (HCOOH): 2.40; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.35 (d,6H, 6H of of CH(CH₃)₂); 2.20 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H ofCH₃); 2.80-3.00 (m, 3H, 3H of CH₂); 3.15 (sept, 1H, 1H of CH(CH₃)₂);5.30-5.80 (each br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.50 (s, 1H,thiophene-H); 8.20 and 8.40 (br, 1H, Pyr-6H); 64 solid, logP (HCOOH):2.71; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.75 (m, 3H, 3H of CH₂); 2.05(m, 1H, 1H of CH₂); 2.25 (s, 6H, 2*3H of thiophene-CH₃); 2.40 (s, 3H, 3Hof pyrimidine-CH₃); 2.45 (m, 1H, 1H of CH₂); 2.65 (m, 1H, 1H of CH₂);5.00- 5.40 (br, 4H, 1H of CH; 2H of NH₂; 1H of NH); 68 solid; 69 solid;m.p.: 129.9° C.; logP (HCOOH): 1.86; 1H NMR (CDCl₃, 400 MHZ, δ in ppm):): 1.85 (m, 3H, 3H of CH₂); 2.15 (m, 1H, 1H of CH₂); 2.70 (m, 2H, 2H ofCH₂); 3.05 (s, 3H, 3H of SO₂—CH₃); 5.25-5.80 (br, 4H, 1H of CH; 2H ofNH₂; 1H of NH); 6.80 (d, 1H, thiophene-H); 7.15 (d, 1H, thiophene-H);8.35 and 8.50 (br, 1H, Pyr-6H); 70 oily 71 solid; logP (HCOOH): 2.98; 1HNMR (CDCl₃, 400 MHZ, δ in ppm): ): 1.85 (m, 3H, 3H of CH₂); 2.10 (m, 1H,1H of CH₂); 2.50 (s, 3H, 3H of acetyl-CH₃); 2.60 and 2.65 (br, 3H, 3H ofpyrimidine-CH₃); 2.80 (m, 2H, 2H of CH₂); 5.30 (br, 1H, 1H of CH); 5.70(br, 1H, 1H of NH); 6.90 (d, 1H, thiophene-H); 7.10 (d, 1H,thiophene-H); 8.65 and 8.80 (br, 1H, Pyr-6H); 72 oily; logP (HCOOH):3.90; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3H of CH₂); 2.05(m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.75 (m, 2H, 2H of CH₂);5.00 to 5.60 and 8.30 to 8.50 (each br, 4H, 1H of CH, 1H of NH; 2H ofNH_(2;) 1H); 6.55 (s, 1H, thiophene-H); 8.60 and 8.80 (2*br, 1H,Pyr-6H); 73 oily; logP (HCOOH): 2.38; 74 logP (HCOOH): 2.13; 1H NMR(CDCl₃, 400 MHZ, δ in ppm): ): 1.85 (m, 2H, 2H of CH₂); 2.10 (m, 2H, 2Hof CH₂); 2.35 (s, 3H, 3H of thiophene-CH₃); 2.60 (s, 3H, 3H ofpyrimidine-CH₃); 2.65 (m, 1H, 1H of CH₂); 2.80 (m, 1H, 1H of CH₂); 5.15(br, 1H, 1H of CH); 5.90 (br, 2H, 2H of NH₂); 6.40 (d, 1H, thiophene-H);76 solid; logP (HCOOH): 3.01; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): ): 1.40(s, 9H, 3*3H C(CH₃)₃); 1.85 (m, 3H, 3H of CH₂); 2.05 (m, 1H, 1H of CH₂);2.40 (s, 3H, 3H of thiophene-CH₃); 2.75 (m, 2H, 2H of CH₂); 5.00-5.70(each br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.55 (d, 1H, thiophene-H);8.30 and 8.45 (br, 1H, Pyr-6H); 77 solid; logP (HCOOH): 2.67; 1H NMR(CDCl₃, 400 MHZ, δ in ppm): 1.40 (s, 9H, 3*3H C(CH₃)₃); 2.10 (m, 1H, 1Hof CH₂); 2.40 (s, 3H, 3H of thiophene-CH₃); 2.80-3.00 (m, 3H, 3H ofCH₂); 5.00-5.70 (each br, 4H, 1H of CH, 1H of NH; 2H of NH₂); 6.55 (d,1H, thiophene-H); 8.20 and 8.40 (br, 1H, Pyr-6H); 80 solid; m.p.: 94.4°C.; logP (HCOOH): 5.60; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H,3H of CH₂); 2.05 (m, 1H, 1H of CH₂); 2.35 (s, 3H, 3H of thiophene- CH₃);2.35 (s, 3H, 3H of thiophene-CH₃); 2.50 and 2.55 (br, 3H, 3H ofpyrimidine- CH₃); 2.70 (m, 2H, 2H of CH₂); 5.15 (br, 1H, 1H of CH); 5.90(br, 1H, 1H of NH); 6.55 (d, 1H, thiophene-H); 8.20 and 8.40 (br, 1H,Pyr-6H); 150 oily; logP (HCOOH): 1.51; 1H NMR (CDCl₃, 400 MHZ, δ inppm): 1.85 (m, 3H, 3H of CH₂); 2.05 (m, 1H, 1H of CH₂); 2.35 (s, 3H, 3Hof CH₃); 2.40 (s, 3H, 3H of CH₃); 2.75 (m, 2H, 2H of CH₂); 5.00 to 5.60and 7.80 to 8.10 (each br, 4H, 1H of CH, 1H of NH; 2H of NH_(2;) 1H);6.55 (s, 1H, thiophene-H); 8.50 to 8.85 (br, 1H, Pyr-6H); 213 solid;m.p.: 190.7° C.; logP (HCOOH): 2.66; 1H NMR (CDCl₃, 400 MHZ, δ in ppm):1.90 (m, 3H, 3H of CH₂); 1.95 (s, 3H, 3H of thiophene-CH₃); 2.05 (m, 1H,1H of CH₂); 2.30 (s, 3H, 3H of thiophene-CH₃); 2.60 (m, 1H, 1H of CH₂);2.75 (m, 1H, 1H of CH₂); 4.80-6.50 (each br, 4H, 1H of CH, 1H of NH; 2Hof NH₂); 7.70 and 8.20 (br, 1H, Pyr-6H); 215 oily; logP (HCOOH): 1.66;1H NMR (CDCl₃, 400 MHZ, δ in ppm): 2.25 (m, 1H, 1H of CH₂); 2.85 (m, 1H,1H of CH₂); 3.00 (m, 2H, 2H of CH₂); 4.90-6.30 (each br, 4H, 1H of CH,1H of NH; 2H of NH₂); 6.90 (d, 1H, thiophene-H); 7.20 (d, 1H, thiophene-H); 7.90 and 8.30 (br, 1H, Pyr-6H); 223 solid; logP (HCOOH): 2.57; 1HNMR (CDCl₃, 400 MHZ, δ in ppm): 1.90 (m, 3H, 3H of CH₂); 2.05 (m, 1H, 1Hof CH₂); 2.80 (m, 2H, 2H of CH₂); 5.10 (m, 1H, 1H of CH); 5.30 (br, 1H,1H of NH); 6.90 (d, 1H, 1H of thiophene-H); 7.10 (d, 1H, 1H ofthiophene-H); 8.20 (s, 2H, 2H of Pyr-4H and Pyr-6H); 224 solid; logP(HCOOH): 3.12; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.90 (m, 3H, 3H ofCH₂); 2.05 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.75 (m, 2H, 2Hof CH₂); 5.00 (m, 1H, 1H of CH); 5.35 (br, 1H, 1H of NH); 6.50 (s, 1H,1H of thiophene-H); 8.15 (s, 2H, 2H of Pyr-4H and Pyr-6H); 240 solid;m.p.: 118.0° C.; logP (HCOOH): 4.55; 1H NMR (CDCl₃, 400 MHZ, δ in ppm):1.40 (t, 3H, 3H of CH₃); 1.85 (m, 3H, 3H of CH₂); 2.10 (m, 1H, 1H ofCH₂); 2.35 (s, 3H, 3H of CH₃); 2.55 to 2.80 (m, 5H, 3H ofpyrimidine-CH_(3;) 2H of CH₂); 5.15 and 5.70 (each br, 2H, 1H of NH; 1Hof CH); 6.55 (s, 1H, thiophene-H); 8.70 and 8.90 (each br, 1H, Pyr-6H);256 solid; logP (HCOOH): 2.30; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 2.15(m, 1H, 1H of CH₂); 2.45 (s, 3H, 3H of thiophene-CH₃); 2.80 to 3.00 (m,3H, 3H of CH₂); 4.90 to 5.70 (br, 4H, 1H of CH; 1H of NH; 2H of NH₂),6.70 (s, 1H, thiophene-H); 8.10 (br, 1H, Pyr-6H); 257 oily; logP(HCOOH): 2.02; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 2.10 (m, 1H, 1H ofCH₂); 2.80 to 3.05 (m, 3H, 3H of CH₂); 4.90 to 5.70 (br, 4H, 1H of CH;1H of NH; 2H of NH₂), 6.55 (s, 1H, thiophene-H); 8.00 to 8.30 (br, 1H,Pyr-6H); 258 solid; m.p.: 155.9° C.; logP (HCOOH): 2.65; 1H NMR (CDCl₃,400 MHZ, δ in ppm): 1.80 to 2.20 (m, 4H, 4H of CH₂); 2.50 (s, 3H, 3H ofacetyl-CH₃); 2.60 to 2.80 (m, 5H, 2H of CH₂; 3H of pyrimidine-CH₃); 5.25and 6.20 (br, 2H, 1H of CH; 1H of NH), 6.70 (s, 1H, thiophene-H); 8.65and 8.90 (each br, 1H, Pyr-6H); 263 oily; logP (HCOOH): 4.84; 1H NMR(CDCl₃, 400 MHZ, δ in ppm): 1.60 (m, 4H, 4H of CH₂); 1.80 to 2.05 (m,6H, 6H of CH₂); 2.35 (s, 3H, 3H of CH₃); 2.40 (s, 3H, 3H of CH₃); 2.30to 2.45 (m, 1H, 1H of CH₂); 2.75 (m, 2H, 2H of CH₂); 5.15 and 5.70 (eachbr, 2H, 1H of NH; 1H of CH); 6.20 (s, 1H, pyrido-H); 6.55 (s, 1H,thiophene-H); 8.40 and 8.60 (each br, 1H, Pyr-6H); 264 oily; logP(HCOOH): 2.77; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.90 (m, 3H, 3H ofCH₂); 2.05 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.75 (m, 2H, 2Hof CH₂); 2.90 (s, 3H, 3H of —SO—CH₃); 4.90-5.50 and 7.90 (each br, 4H,1H of CH, 1H of NH; 2H of NH₂); 6.30 (t, 1H, 1H of CF₂H); 6.55 (s, 1H,thiophene-H); 265 oily; logP (HCOOH): 1.35; 1H NMR (CDCl₃, 400 MHZ, δ inppm): 1.90 (m, 3H, 3H of CH₂); 2.05 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3Hof CH₃); 2.75 (m, 2H, 2H of CH₂); 4.80 and 5.10 (each br, 4H, 1H of CH,1H of NH; 2H of NH₂); 6.55 (s, 1H, thiophene- H); 7.05, 7.15, 7.20 and7.40 (each m, 4H, 4H of Ph); 7.90 (s, 1H, Pyr-6H); 266 logP (HCOOH):1.17; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.90 (m, 3H, 3H of CH₂); 2.05(m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃); 2.70 (m, 2H, 2H of CH₂);2.95 (d, 3H, 3H of —HN—CH₃); 5.00 and 5.90 and 6.60-7.00 (each br, 5H,1H of CH, 1H of NH; 1H of CONH; 2H of NH₂); 6.55 (s, 1H, thiophene-H);7.50 and 8.20 (each br, 1H, Pyr-6H); 267 logP (HCOOH): 1.09; 1H NMR(CDCl₃, 400 MHZ, δ in ppm): 1.90 (m, 3H, 3H of CH₂); 2.05 (m, 1H, 1H ofCH₂); 2.40 (s, 3H, 3H of CH₃); 2.70 (m, 2H, 2H of CH₂); 2.95 (d, 3H, 3Hof —HN—CH₃); 5.00 and 5.80 and 6.60-7.60 (each br, 7H, 1H of CH, 1H ofNH; 1H of CONH₂; 2H of NH_(2;) 1H, Pyr-4H); 6.55 (s, 1H, thiophene-H);268 oily; logP (HCOOH): 3.83; 1H NMR (CDCl₃, 400 MHZ, δ in ppm): 1.80(m, 3H, 3H of CH₂); 2.05 (m, 1H, 1H of CH₂); 2.40 (s, 3H, 3H of CH₃);2.50 (s, 3H, 3H of COCH₃); 2.75 (m, 2H, 2H of CH₂); 5.00 to 5.50 and6.00-6.50 (each br, 4H, 1H of CH, 1H of NH; 2H of NH_(2;) 1H); 6.55 (s,1H, thiophene-H); 275 oily; logP (HCOOH): 1.24; 1H NMR (CDCl3, 400 MHZ,δ in ppm): 1.85 (m, 3H, 3H of CH2); 2.05 (m, 1H, 1H of CH2); 2.40 (s,3H, 3H of CH3); 2.75 (m, 2H, 2H of CH2); 4.60 to 5.40 (each br, 4H, 1Hof CH, 1H of NH; 2H of NH2; 1H); 5.70 and 6.15 (2*s, 2*1H, C═C—H); 6.55(s, 1H, thiophene-H); 7.80 (br, 1H, Pyr-6H);

B. FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a    compound of the formula (I) and/or salts thereof and 90 parts by    weight of talc as an inert substance and comminuting the mixture in    a hammer mill.-   b) A readily water-dispersible, wettable powder is obtained by    mixing 25 parts by weight of a compound of the formula (I) and/or    salts thereof, 64 parts by weight of kaolin-containing quartz as an    inert substance, 10 parts by weight of potassium lignosulfonate and    1 part by weight of sodium oleoylmethyltaurate as a wetting agent    and dispersant, and grinding the mixture in a pinned-disk mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) and/or    salts thereof with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range for example about 255 to above 277° C.), and grinding the    mixture in a friction ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I) and/or salts thereof, 75 parts by    weight of cyclohexanone as a solvent and 10 parts by weight of    ethoxylated nonylphenol as an emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium lauryl sulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disk mill, and granulating the        powder in a fluidized bed by spray application of water as a        granulating liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting, in a colloid mill,    -   25 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate    -   2 parts by weight of sodium oleoylmethyltaurate,    -   1 part by weight of polyvinyl alcohol    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water,    -   then grinding the mixture in a bead mill and atomizing and        drying the resulting suspension in a spray tower by means of a        one-phase nozzle.

C. BIOLOGICAL EXAMPLES

Test Description

1. Pre-Emergence Herbicidal Effect and Crop Plant Compatibility

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare laid out in wood-fiber pots in sandy loam and covered with soil. Thecompounds of the invention, formulated in the form of wettable powders(WP) or as emulsion concentrates (EC), are then applied to the surfaceof the covering soil as aqueous suspension or emulsion at a waterapplication rate equating to 600 to 800 L/ha with addition of 0.2%wetting agent.

After the treatment, the pots are placed in a greenhouse and kept undergood growth conditions for the trial plants. The damage to the testplants is scored visually after a test period of 3 weeks by comparisonwith untreated controls (herbicidal activity in percent (%): 100%activity=the plants have died, 0% activity=like control plants).

In the tables below, the following abbreviations are used:

Undesired Plants/Weeds:

-   -   ABUTH: Abutilon theophrasti ALOMY: Alopecurus myosuroides    -   AMARE: Amaranthus retroflexus AVEFA: Avena fatua    -   CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli    -   LOLMU: Lolium multiflorum MATIN: Matricaria inodora    -   PHBPU: Ipomoea purpurea POLCO: Polygonum convolvulus    -   SETVI: Setaria viridis STEME: Stellaria media    -   VERPE: Veronica persica VIOTR: Viola tricolor

TABLE 3 (pre-emergence efficacy): Dos- Ex. age No [g/ha] ALOMY AVEFACYPES ECHCG LOLMU SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VERPE VIOTR2 320 80 100 100 4 320 100 100 100 100 100 100 100 100 100 100 4 80 100100 100 100 100 100 7 320 100 90 90 100 7 80 80 8 320 80 100 100 100 100100 100 100 100 100 8 80 90 90 100 100 100 80 100 100 9 320 100 100 100100 100 100 100 100 100 9 80 100 80 100 100 100 100 100 100 90 10 320 80100 100 11 320 100 90 100 100 100 100 100 100 100 100 100 11 80 90 60100 100 100 100 100 100 100 100 100 100 12 320 90 90 90 90 80 100 100100 13 320 100 100 100 90 100 16 320 100 100 40 100 100 40 100 100 10016 80 100 20 40 90 100 20 100 100 100 17 320 100 100 100 100 100 100 100100 100 100 17 80 100 60 80 100 100 100 100 100 19 320 100 80 100 100100 100 100 80 100 100 100 19 80 100 100 80 100 100 100 100 100 22 320100 100 100 80 100 100 100 100 100 100 23 320 80 90 100 100 100 100 100100 100 100 100 100 23 80 100 100 100 100 100 100 24 320 100 90 60 100100 100 100 100 100 100 100 100 100 100 24 80 100 90 100 100 100 100 100100 27 320 100 100 100 100 100 27 80 90 28 320 90 100 100 80 100 100 100100 100 100 28 80 100 90 100 100 90 29 320 100 100 100 100 100 100 100100 90 100 29 80 90 60 100 100 100 30 320 90 100 100 100 100 100 30 8090 100 90 90 100 33 320 100 100 100 100 100 100 100 100 33 80 100 100100 80 100 35 320 90 90 90 100 90 100 36 320 100 100 100 100 100 36 80100 100 100 90 100 38 320 90 100 90 39 320 100 100 80 100 100 90 100 100100 39 80 80 100 100 80 100 100 42 320 100 100 100 100 100 80 100 100100 42 80 100 100 100 100 100 100 100 44 320 100 100 100 100 100 100 100100 100 100 44 80 80 100 100 100 100 100 100 100 46 320 100 100 100 10080 100 100 100 100 100 100 100 46 80 100 100 80 100 100 100 90 100 100100 47 320 100 100 80 100 100 100 100 100 100 100 100 100 100 100 47 8080 100 100 80 100 100 100 100 100 100 100 48 320 80 100 80 100 90 100100 100 48 80 100 80 100 100 49 320 100 100 70 100 49 80 90 100 50 320100 80 100 100 90 100 100 100 100 50 80 90 100 90 100 100 80 52 320 8090 100 90 100 100 100 100 100 100 100 100 52 80 70 90 100 80 80 90 100100 100 100 100 53 320 100 100 100 100 90 100 100 100 53 80 100 100 10080 100 100 55 320 100 100 100 100 100 100 100 100 90 100 100 100 55 8090 100 100 100 100 100 100 100 100 59 320 80 80 100 90 100 100 100 100100 100 100 100 59 80 100 80 80 100 100 80 100 100 100 61 320 100 80 90100 100 100 100 90 90 100 100 100 61 80 80 90 100 30 100 100 90 90 10080 62 320 60 80 50 80 90 100 100 100 90 100 62 80 80 90 90 63 320 100100 100 100 100 100 63 80 100 20 100 100 69 320 80 100 100 100 100 100100 100 100 100 100 69 80 100 100 100 100 100 70 320 100 100 100 100 100100 100 100 100 70 80 100 100 100 100 90 100 72 320 90 80 100 100 100100 100 100 100 72 80 80 80 100 100 100 73 320 90 100 100 100 100 100100 100 100 100 100 73 80 80 100 80 100 100 100 100 100 80 320 70 60 100100 90 100 100 100 100 80 80 100 100 70 100 100 100 90 150 320 100 100100 100 70 100 100 100 100 100 150 80 90 90 100 100 100 100 70 100 173320 80 60 60 100 100 100 100 100 100 100 100 100 100 173 80 60 100 60 90100 100 90 100 90 100 213 320 100 100 80 100 100 100 100 100 100 100 100100 100 213 80 100 80 90 80 100 100 100 90 100 100 100 215 320 90 70 100100 100 100 100 100 100 100 90 215 80 70 80 90 100 100 100 100 80 240320 60 100 70 80 100 10 70 100 100 100 240 80 90 90 70 100 100 70 256320 100 100 100 100 100 100 100 100 100 100 100 100 256 80 60 100 100100 100 100 100 100 100 257 320 100 100 100 100 100 100 100 100 100 100100 100 100 257 80 100 100 100 100 70 100 100 100 100 100 100 259 320100 100 100 80 260 320 90 90 100 100 100 100 100 100 100 100 100 260 8070 50 50 100 100 80 100 100 100 264 320 60 100 100 60 90 100 100 100 100100 100 264 80 60 80 100 90 100 100 100 265 320 100 60 100 100 265 80100 266 320 100 60 100 100 100 100 100 100 266 80 100 100 100 100 267320 80 90 80 100 100 100 100 267 80 80 100 100 100 90 268 320 90 90 10090 100 100 90 268 80 80 90 100 90 100 80 271 320 90 100 100 80 275 32080 100 60 100 100 100 70 100 100 100 275 80 80 90 70 90 100 100 100 282320 100 90 100 100 100 100 80 100 100 100 100 100 100 282 80 100 80 80100 100 100 80 100 100 100 100 100 100 283 320 100 80 100 100 100 100100 100 100 100 100 100 100 283 80 80 100 100 100 90 100 100 60 100 100100 284 320 80 70 100 100 100 80 100 100 50 100 100 284 80 70 50 90 80100 20 100 100 50 90 100 285 320 60 50 100 90 100 100 100 100 100 100100 285 80 50 60 80 70 100 100 100 100 100 286 320 60 70 100 80 100 60100 100 50 100 100 100 100 286 80 70 80 100 60 100 100 287 320 100 100100 100 100 100 287 80 80 100 90 90 100 90 288 320 80 100 100 100 70 100100 100 100 100 100 288 80 100 80 100 100 70 290 320 80 100 100 100 100100 80 100 100 100 290 80 60 90 50 100 100 100 291 320 90 80 60 100 100100 100 70 100 100 100 291 80 60 90 100 100 100 90 292 320 100 100 70100 100 100 100 100 100 292 80 80 70 100 100 100 293 320 70 80 60 100100 100 100 100 100 293 80 70 100 294 320 100 100 100 80 100 100 90 29480 70 90 70 100 100 80 296 320 100 100 90 100 100 296 80 70 90 100 60297 320 100 100 100 90 297 80 90 80 100 70 298 320 90 100 100 50 100 100100 298 80 100 100 90 299 320 100 90 100 90 100 300 320 70 100 90 100100 300 80 80 80 301 320 80 70 100 100 100 100 100 100 100 100 301 80 70100 100 100 100 100 100 302 320 70 100 100 80 100 100 80 100 100 302 8070 100 90 60 70 100 303 320 100 90 60 100 100 90 303 80 100 80 100 10070 304 320 60 100 100 304 80 100 307 320 60 50 70 100 309 320 90 90 90100 80 100 100 100 100 100 100 309 80 60 90 90 90 100 100 100 100 310320 90 100 314 320 60 90 100 100 100 314 320 90 60 90 100 60 100 100 100100 100 100 314 80 60 70 100 90 90 100 100 100 316 320 100 80 70 100 100100 318 320 100 100 90 100 100 100 100 320 320 100 100 100 100 100 100100 341 320 70 100 100 70 100 100 100 100 100 100 341 80 60 90 100 10070 100 100 100 342 320 70 100 100 100 342 80 100 100 352 320 60 100 10090 60 100 100 100 352 80 90 60 100 100 80

As shown by the results, the compounds of the invention have goodherbicidal pre-emergence activity against a broad spectrum of weedgrasses and broad-leaved weeds. For example, the compounds from Table 3have very good herbicidal activity against harmful plants such as Avenafatua, Stellaria media, Echinochloa crus-galli, Lolium multiflorum,Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus andAlopecurus myosuroides when applied by the pre-emergence method at anapplication rate of 0.32 kg or less of active substance per hectare. Thecompounds of the invention are therefore suitable for control ofunwanted plant growth by the pre-emergence method.

2. Post-Emergence Herbicidal Effect and Crop Plant Compatibility

Seeds of monocotyledonous and dicotyledonous weed and crop plants arelaid out in sandy loam in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Thecompounds of the invention, formulated in the form of wettable powders(WP) or as emulsion concentrates (EC), are then sprayed onto the greenparts of the plants as aqueous suspension or emulsion at a waterapplication rate equating to 600 to 800 L/ha with addition of 0.2%wetting agent. After the test plants have been left to stand in thegreenhouse under optimal growth conditions for about 3 weeks, the actionof the preparations is assessed visually in comparison to untreatedcontrols (herbicidal action in percent (%): 100% activity=the plantshave died, 0% activity=like control plants).

TABLE 4 (post-emergence efficacy): Dos- Ex. age: No [g/ha] ALOMY AVEFAECHCG LOLMU SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VERPE VIOTR 4 320100 90 100 100 4 80 80 7 320 40 80 8 320 100 80 90 90 90 90 8 80 80 9320 80 100 80 80 90 80 90 90 90 9 80 80 80 80 80 11 320 90 80 100 90 10090 100 90 90 100 90 100 11 80 100 90 100 90 90 90 90 90 80 100 13 320 8090 100 16 320 100 90 90 90 80 90 17 320 90 100 100 100 100 100 100 80 080 100 100 90 17 80 80 90 80 19 320 90 100 80 100 90 90 100 100 100 1980 100 90 90 80 80 90 90 22 320 90 90 100 90 90 90 90 23 320 80 80 80100 80 80 90 90 100 23 80 80 80 80 90 80 24 320 80 100 90 100 100 80 100100 100 24 80 100 90 80 80 80 90 90 28 320 100 90 29 320 100 80 100 90100 90 29 80 90 90 80 30 80 90 30 80 33 320 90 90 33 80 80 35 320 80 9036 320 80 80 100 36 80 100 38 320 80 90 39 320 80 80 39 80 80 42 320 10090 80 100 100 100 42 80 90 90 90 44 320 90 100 100 90 100 100 80 100 10080 46 320 100 80 100 100 90 40 100 80 90 100 100 100 46 80 90 100 80 90100 90 100 80 80 47 320 100 90 100 80 90 90 90 100 100 80 100 100 47 80100 100 90 90 90 100 80 100 100 100 48 320 100 90 90 80 90 80 90 48 8080 80 80 49 320 90 49 80 80 50 320 90 100 90 100 50 80 80 80 90 52 320100 80 100 60 100 90 90 52 80 60 100 60 100 90 90 53 320 90 100 100 9090 100 90 100 53 80 80 90 80 100 90 90 55 320 90 100 90 90 90 100 100 90100 100 100 55 80 90 100 80 90 90 90 100 90 100 90 90 59 320 100 90 2090 80 100 80 59 80 20 90 20 60 80 90 80 61 320 100 100 90 90 90 90 100100 90 100 100 90 61 80 100 80 90 90 90 80 100 100 90 62 320 40 80 90 90100 62 80 80 63 320 40 90 63 80 10 90 69 320 80 80 80 90 90 80 100 69 8020 80 70 320 80 100 100 100 70 80 40 100 72 320 80 80 100 72 80 80 80 73320 100 80 100 100 100 60 73 80 100 90 80 80 320 70 90 90 100 90 100 60100 100 100 80 80 70 80 100 70 90 100 90 100 150 320 80 90 90 80 90 9090 100 100 90 150 80 80 80 80 80 100 80 173 320 100 90 100 90 90 90 9090 100 60 100 100 90 173 80 100 60 80 80 90 60 90 100 90 213 320 90 8090 80 90 90 90 90 90 90 90 90 100 213 80 80 80 50 80 80 80 80 90 256 32090 70 100 70 90 90 100 100 100 90 100 90 256 80 100 90 90 100 100 90 10090 257 320 90 100 100 100 90 90 90 90 90 80 100 100 90 257 80 70 70 90100 90 90 80 90 80 60 80 90 260 320 100 70 100 90 90 90 90 60 100 100 90260 80 80 90 70 70 60 80 70 264 320 90 80 90 90 90 80 100 90 90 264 8090 80 100 90 90 265 320 80 60 90 80 265 80 80 60 90 80 266 320 60 80 10060 100 90 90 266 80 80 90 60 80 90 80 267 320 60 80 80 80 80 100 80 90267 80 80 80 80 80 80 80 268 320 80 100 80 80 268 80 100 80 80 275 32080 90 70 90 90 90 275 80 70 80 90 70 282 320 100 100 100 100 100 90 10090 90 90 100 90 100 282 80 100 100 100 100 100 90 100 90 80 90 100 80100 283 320 90 80 100 100 90 90 100 90 90 70 100 100 100 283 80 80 50 9090 90 80 100 90 284 320 100 80 100 90 80 80 100 100 100 90 284 80 90 9080 90 100 60 285 320 100 80 60 100 80 100 285 80 100 90 60 80 286 320 9090 90 70 100 100 90 286 80 90 90 80 70 70 90 287 320 80 80 100 100 100100 287 80 80 90 80 80 100 288 320 70 60 90 90 90 70 70 80 100 90 288 8070 290 320 60 60 80 90 100 90 290 80 60 80 80 60 291 320 80 90 80 80 6080 291 80 60 80 80 292 320 80 80 30 90 80 293 320 90 100 90 90 293 80 8080 70 294 320 70 70 90 294 80 60 70 296 320 70 70 90 60 90 80 296 80 4060 70 298 320 90 80 298 80 70 80 299 320 90 300 320 70 90 60 90 300 8060 301 320 80 60 90 60 100 90 301 80 80 60 80 302 320 60 80 90 302 80 90314 320 60 60 70 90 50 60 316 320 100 80 320 320 80 60 80 60 60 100 100341 320 70 60 90 90 90 90 60 100 90 341 80 80 80 60 80 90 352 320 80 90100 90 352 80 80 80

As the results show, compounds according to the invention have goodherbicidal post-emergence efficacy against a broad spectrum of weedgrasses and broad-leaved weeds. For example, the compounds from table 4have very good herbicidal activity against harmful plants such as Avenafatua, Stellaria media, Echinochloa crus-galli, Lolium multiflorum,Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus andAlopecurus myosuroides when applied by the post-emergence method at anapplication rate of 0.32 kg or less of active substance per hectare. Thecompounds of the invention are therefore suitable for control ofunwanted plant growth by the post-emergence method.

The invention claimed is:
 1. A compound of formula (I)

and/or an agrochemically acceptable salt thereof, where A¹, A² and A³each independently of one another, are selected from the groupconsisting of O, S, CR⁹, CR¹⁰ and CR¹¹, where exactly one atom of A¹, A²and A³ represents O or S; R⁹, R¹⁰ and R¹¹ each independently of oneanother, are selected from the group consisting of hydrogen, halogen,cyano, C(O)OH, C(O)NH₂, (C₁-C₆)-alkyl, (C₁-C₆)-alkylcarbonyl,(C₁-C₆)-alkyloxycarbonyl, (C₁-C₆)-alkylaminocarbonyl,(C₁-C₆)-dialkylaminocarbonyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy,(C₁-C₆)-haloalkoxy, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₂-C₆)-alkynylcarbonyl,(C₂-C₆)-haloalkynylcarbonyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyloxy,(C₂-C₆)-alkynyloxycarbonyl, (C₂-C₆)-haloalkynyloxycarbonyl and nitro; R¹and R² each independently of one another, are selected from the groupconsisting of halogen, hydroxy, nitro, amino, cyano, C(O)NH₂;(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl,(C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,(C₁-C₆)-haloalkylcarbonyloxy, (C₁-C₆)-alkylcarbonyl-(C₁-C₄)-alkyl;(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-haloalkyl; (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkenylcarbonyl,(C₂-C₆)-haloalkenylcarbonyl, (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyloxy,(C₂-C₆)-alkenyloxycarbonyl, (C₂-C₆)-haloalkenyloxycarbonyl;(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-alkynylcarbonyl,(C₂-C₆)-haloalkynylcarbonyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyloxy,(C₂-C₆)-alkynyloxycarbonyl, (C₂-C₆)-haloalkynyloxycarbonyl;tri-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,di-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,mono-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl; phenylsilyl-(C₂-C₆)-alkynyl;(C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy, (C₆-C₁₄)-arylcarbonyl and(C₆-C₁₄)-aryloxycarbonyl which may each be substituted at the arylmoiety by halogen, (C₁-C₆)-alkyl and/or (C₁-C₆)-haloalkyl;(C₆-C₁₄)-aryl-(C₁-C₆)-alkyl, (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxy,(C₆-C₁₄)-aryl-(C₁-C₆)-alkyl-carbonyl,(C₆-C₁₄)-aryl-(C₁-C₆)-alkyl-carbonyloxy,(C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyl,(C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyloxy; aminocarbonyl-(C₁-C₆)-alkyl,di-(C₁-C₆)-alkylaminocarbonyl-(C₁-C₆)-alkyl;N—((C₁-C₆)-haloalkanoyl)-amino-carbonyl,mono-((C₆-C₁₄)-aryl)-amino-carbonyl, di-((C₆-C₁₄)-aryl)-amino-carbonyl;(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy; (C₃-C₈)-cycloalkyl, which mayoptionally be substituted at the cycloalkyl radical by (C₁-C₆)-alkyland/or halogen; (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxy, (C₃-C₈)-cycloalkylcarbonyl,(C₃-C₈)-cycloalkoxycarbonyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyl,(C₃-C₈)-cycloalkylcarbonyloxy, (C₃-C₈)-cycloalkoxycarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyloxy; (C₃-C₈)-cycloalkenyl,(C₃-C₈)-cycloalkenyloxy, (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxy, (C₃-C₈)-cycloalkenylcarbonyl,(C₃-C₈)-cycloalkenyloxycarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyl,(C₃-C₈)-cycloalkenylcarbonyloxy, (C₃-C₈)-cycloalkenyloxycarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyloxy;hydroxy-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkoxy, cyano-(C₁-C₆)-alkoxy,cyano-(C₁-C₆)-alkyl; and (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio,(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-haloalkylthio,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-haloalkyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-haloalkylsulfonyloxy, (C₁-C₆)-alkylthiocarbonyl,(C₁-C₆)-haloalkylthiocarbonyl, (C₁-C₆)-alkylthiocarbonyloxy,(C₁-C₆)-haloalkylthiocarbonyloxy, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkoxy,(C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyloxy; (C₄-C₁₄)-arylsulfonyl,(C₆-C₁₄)-arylthio, (C₆-C₁₄)-arylsulfinyl, (C₃-C₈)-cycloalkylthio,(C₃-C₈)-alkenylthio, (C₃-C₈)-cycloalkenylthio and (C₃-C₆)-alkynylthio;R³ is selected from the group consisting of hydrogen, halogen, hydroxy,nitro, amino, cyano, C(O)OH, C(O)NH₂; (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-haloalkylcarbonyloxy,(C₁-C₆)-alkylcarbonyl-(C₁-C₄)-alkyl; (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,(C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-haloalkyl; (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkenylcarbonyl,(C₂-C₆)-haloalkenylcarbonyl, (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyloxy,(C₂-C₆)-alkenyloxycarbonyl, (C₂-C₆)-haloalkenyloxycarbonyl;(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-alkynylcarbonyl,(C₂-C₆)-haloalkynylcarbonyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyloxy,(C₂-C₆)-alkynyloxycarbonyl, (C₂-C₆)-haloalkynyloxycarbonyl;tri-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,di-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,mono-(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl; phenylsilyl-(C₂-C₆)-alkynyl;(C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy, (C₆-C₁₄)-arylcarbonyl and(C₆-C₁₄)-aryloxycarbonyl which may each be substituted at the arylmoiety by halogen, (C₁-C₆)-alkyl and/or (C₁-C₆)-haloalkyl;(C₆-C₁₄)-aryl-(C₁-C₆)-alkyl, (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxy,(C₆-C₁₄)-aryl-(C₁-C₆)-alkyl-carbonyl,(C₆-C₁₄)-aryl-(C₁-C₆)-alkyl-carbonyloxy,(C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyl,(C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyloxy; aminocarbonyl-(C₁-C₆)-alkyl,di-(C₁-C₆)-alkylaminocarbonyl-(C₁-C₆)-alkyl;N—((C₁-C₆)-haloalkanoyl)-amino-carbonyl,mono-((C₆-C₁₄)-aryl)-amino-carbonyl, di-((C₆-C₁₄)-aryl)-amino-carbonyl;(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy; (C₃-C₈)-cycloalkyl, which mayoptionally be substituted at the cycloalkyl radical by (C₁-C₆)-alkyland/or halogen; (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxy, (C₃-C₈)-cycloalkylcarbonyl,(C₃-C₈)-cycloalkoxycarbonyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyl,(C₃-C₈)-cycloalkylcarbonyloxy, (C₃-C₈)-cycloalkoxycarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyloxy; (C₃-C₈)-cycloalkenyl,(C₃-C₈)-cycloalkenyloxy, (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxy, (C₃-C₈)-cycloalkenylcarbonyl,(C₃-C₈)-cycloalkenyloxycarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyl,(C₃-C₈)-cycloalkenylcarbonyloxy, (C₃-C₈)-cycloalkenyloxycarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyloxy;hydroxy-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkoxy, cyano-(C₁-C₆)-alkoxy,cyano-(C₁-C₆)-alkyl; and (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio,(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-haloalkylthio,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-haloalkyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-haloalkylsulfonyloxy, (C₁-C₆)-alkylthiocarbonyl,(C₁-C₆)-haloalkylthiocarbonyl, (C₁-C₆)-alkylthiocarbonyloxy,(C₁-C₆)-haloalkylthiocarbonyloxy, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkoxy,(C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyloxy; (C₄-C₁₄)-arylsulfonyl,(C₆-C₁₄)-arylthio, (C₆-C₁₄)-arylsulfinyl, (C₃-C₈)-cycloalkylthio,(C₃-C₈)-alkenylthio, (C₃-C₈)-cycloalkenylthio, and (C₃-C₆)-alkynylthio;or R¹ may be attached to R² via a bond, resulting in a 5- to 7-memberedpartially hydrogenated carbocycle or heterocycle having at least oneheteroatom selected from the group consisting of N, O, S and P, whichcarbocycle or heterocycle is optionally substituted by one or moresubstituents selected from the group consisting of hydroxy, ═O, ═N—O—H,═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl substitutedby one or more identical or different halogen atoms, (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl and (C₁-C₆)-haloalkyl, and R⁴ is selected from thegroup consisting of hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxycarbonyl and aminocarbonyl;R⁵ and R⁶ each independently of one another, are selected from the groupconsisting of hydrogen, hydroxy, (C₁-C₆)-alkyl, (C₁-C₆)-alkylphenyl,(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy and (C₁-C₆)-haloalkoxy; or theradicals R⁵ and R⁶ together with the carbon atom to which they areattached form a 3- to 7-membered ring; R⁷ and R⁸ each independently ofone another, are selected from the group consisting of hydrogen,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,(C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy, (C₆-C₁₄)-arylcarbonyl and(C₆-C₁₄)-aryloxycarbonyl; or the radicals R⁷ and R⁸ together form a(C₁-C₇)-alkylene group which may contain one or more oxygen and/orsulfur atoms, where the (C₁-C₇)-alkylene group may be mono- orpolysubstituted by halogen and the respective halogen substituents maybe identical or different; X represents a bond or is selected from thegroup consisting of O, S, CH₂, C═O, NH, CR¹²R¹³, NR¹⁴, CH₂O and CH₂S,wherein X is not a bond when n=0, and when X is CH₂O or CH₂S the carbonatom is attached to the aromatic moiety and the heteroatom O or S isattached to CR⁵R⁶ when n=0 and CR⁷R⁸ when n=1 or 2; R¹² and R¹³ eachindependently of one another, are selected from the group consisting ofhydrogen, (C₁-C₆)-alkyl and (C₁-C₆)-haloalkyl; R¹⁴ is selected from thegroup consisting of hydrogen, (C₁-C₆)-alkyl and (C₁-C₆)-haloalkyl; and nrepresents the number 0, 1 or
 2. 2. The compound of formula (I) and/orsalt as claimed in claim 1, wherein A¹, A² and A³, each independently ofone another, are selected from the group consisting of S, CR⁹, CR¹⁰ andCR¹¹, where exactly one atom of A¹, A² and A³ represents S.
 3. Thecompound of formula (I) and/or salt as claimed in claim 1 wherein theradicals R⁹, R¹⁰ and R¹¹, each independently of one another, areselected from the group consisting of hydrogen, halogen and(C₁-C₆)-alkyl.
 4. The compound of formula (I) and/or salt as claimed inclaim 1, wherein A¹, A² and A³, each independently of one another, areselected from the group consisting of S, CR⁹, CR¹⁰ and CR¹¹, whereexactly one atom of A¹, A² and A³ represents S, and R⁹, R¹⁰ and R¹¹,each independently of one another, are selected from the groupconsisting of hydrogen, chlorine and (C₁-C₃)-alkyl.
 5. The compound offormula (I) and/or salt as claimed in claim 1, wherein exactly oneradical R⁹, R¹⁰ or R¹¹ represents methyl and the other radicalsrepresent hydrogen.
 6. The compound of formula (I) and/or salt asclaimed in claim 1, wherein the radicals R¹ and R², each independentlyof one another, are selected from the group consisting of halogen,hydroxy, nitro, amino, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio,(C₁-C₆)-alkylsulfinyl and (C₁-C₆)-haloalkylsulfonyl and R³ is selectedfrom the group consisting of hydrogen, halogen, hydroxy, nitro, amino,cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl,(C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl and(C₁-C₆)-haloalkylsulfonyl.
 7. The compound of formula (I) and/or salt asclaimed in claim 1, wherein R¹ is amino, R² is trifluoromethyl ormethylsulfonyl, and R³ is hydrogen or methyl.
 8. The compound of formula(I) and/or salt as claimed in claim 1, wherein the radical R¹ isattached to R² via a bond, resulting in a 5- or 6-membered partiallyhydrogenated carbocycle or heterocycle having at least one heteroatomselected from the group consisting of N, O, S and P, which carbocycle orheterocycle is optionally substituted by one or more substituentsselected from the group consisting of hydroxy, ═O, ═N—O—H,═N—O—(C₁-C₆)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl substitutedby one or more identical or different halogens, (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl and (C₁-C₆)-haloalkyl, and R³ is selected from thegroup consisting of hydrogen, amino, methyl and trifluoromethyl.
 9. Thecompound of formula (I) and/or salt as claimed in claim 1, wherein theradical R⁴ is selected from the group consisting of hydrogen, CH₃,CH₂CH₂OCH₃, COOCH₃ and CONH₂.
 10. The compound of formula (I) and/orsalt as claimed in claim 1, wherein the radicals R⁵ and R⁶, eachindependently of one another, are selected from the group consisting ofhydrogen, hydroxy, (C₁-C₆)-alkyl, (C₁-C₆)-alkylphenyl and(C₁-C₆)-alkoxy.
 11. The compound of formula (I) and/or salt as claimedin claim 1, wherein the radicals R⁷ and R⁸, each independently of oneanother, are selected from the group consisting of hydrogen,(C₁-C₆)-alkyl and (C₆-C₁₄)-aryl.
 12. The compound of formula (I) and/orsalt as claimed in claim 1, wherein X represents a bond or is selectedfrom the group consisting of O, S, CH₂, C═O, NH, CHCH₃, NCH₃, C(CH₃)₂,OCH₂ and SCH₂, wherein X is not a bond when n=0, and when X is CH₂O orCH₂S the carbon atom is attached to the aromatic moiety and theheteroatom 0 or S is attached to the CR⁵R⁶ when n=0, and CR⁷R⁸ when n=1or
 2. 13. The compound of formula (I) and/or salt as claimed in claim 1,wherein the number n represents 1 or
 2. 14. The compound of formula (I)and/or salt as claimed in claim 1, wherein R¹ and R² each independentlyof one another, are selected from the group consisting of amino,trifluoromethyl (C₁-C₃)-alkyl, and (C₁-C₆)-alkylsulfonyl; and R³ isselected from the group consisting of hydrogen, amino, trifluoromethyl,(C₁-C₆)-alkyl, and (C₁-C₆)-alkylsulfonyl; or R¹ is attached to R² via abond, resulting in a 5- or 6-membered partially hydrogenated carbocycleor heterocycle having at least one heteroatom selected from the groupconsisting of N, O, S and P, which carbocycle or heterocycle isoptionally substituted by one or more substituents selected from thegroup consisting of hydroxy, ═O, ═N—O—H, ═N—O—(C₁-C₆)-alkyl,═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl substituted by one or morehalogen atoms, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl and (C₁-C₆)-haloalkyl;and R³ is selected from the group consisting of hydrogen, methyl, aminoand trifluoromethyl; R⁴ is selected from the group consisting ofhydrogen, CH₃, CH₂CH₂OCH₃, COOCH₃ and CONH₂; R⁵ and R⁶ eachindependently of one another, are selected from the group consisting ofhydrogen, (C₁-C₃)-alkyl and (C₁-C₆)-alkoxy; R⁷ and R⁸ each independentlyof one another, are selected from the group consisting of hydrogen,(C₁-C₆)-alkyl and (C₆-C₁₄)-aryl; A¹, A² and A³ each independently of oneanother, are selected from the group consisting of S, CR⁹, CR¹⁰, CR¹¹,where exactly one atom of A¹, A² and A³ represents S; R⁹, R¹⁰ and R¹¹each independently of one another, are selected from the groupconsisting of hydrogen, halogen and (C₁-C₆)-alkyl; X represents a bondor is selected from the group consisting of O, S, CH₂, ═O, NH, CHCH₃,NCH₃, C(CH₃)₂, OCH₂ and SCH₂, wherein X is not a bond when n=0, and whenX is CH₂O or CH₂S the carbon atom is attached to the aromatic moiety andthe heteroatom O or S is attached to CR⁵R⁶ when n=0 and CR⁷R⁸ when n=1or 2; and n represents the number 1 or
 2. 15. A compound of formula (I)

and/or salt as claimed in claim 1, wherein the chiral carbon atomindicated by (*) has (R) configuration.
 16. A compound of formula (I)

and/or salt as claimed in claim 1, wherein the chiral carbon atomindicated by (*) has (R) configuration and the chiral carbon atomindicated by (**) has (S) configuration.
 17. A product comprising one ormore compounds of formula (I)

and/or agrochemically acceptable salts thereof, where A¹, A² and A³ eachindependently of one another, are selected from the group consisting ofS, CR⁹, CR¹⁰ and CR¹¹, where exactly one atom of A¹, A² and A³represents S; R⁹, R¹⁰ and R¹¹ each independently of one another, areselected from the group consisting of hydrogen, halogen and(C₁-C₆)-alkyl; R¹, R² and R³ each independently of one another, areselected from the group consisting of hydrogen, amino, trifluoromethyl,(C₁-C₆)-alkyl and (C₁-C₆)-alkylsulfonyl; or R¹ may be attached to R² viaa bond, resulting in a 5- to 6-membered partially hydrogenatedcarbocycle or heterocycle having at least one heteroatom selected fromthe group consisting of N, O, S and P, which carbocycle or heterocycleis optionally substituted by one or more substituents selected from thegroup consisting of hydroxy, ═O, ═N—O—H, ═N—O—(C₁-C₆)-alkyl,═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl substituted by one or moreidentical or different halogen atoms, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyland (C₁-C₆)-haloalkyl, and R⁴ is selected from the group consisting ofhydrogen, CH₃, CH₂CH₂OCH₃, COOCH₃ and CONH₂; R⁵ and R⁶ eachindependently of one another, are selected from the group consisting ofhydrogen, (C₁-C₃)-alkyl and (C₁-C₆)-alkoxy; R⁷ and R⁸ each independentlyof one another, are selected from the group consisting of hydrogen,(C₁-C₆)-alkyl and (C₆-C₁₄)-aryl; X represents a bond or is selected fromthe group consisting of O, S, CH₂, C═O, NH, CHCH₃, NCH₃, C(CH₃)₂, CH₂Oand CH₂S, wherein X is not a bond when n=0, and when X is CH₂O or CH₂Sthe carbon atom is attached to the aromatic moiety and the heteroatom Oor S is attached to CR⁵R⁶ when n=0 and CR⁷R⁸ when n=1 or 2; and nrepresents the number 0, 1 or
 2. 18. A process for preparing a compoundof formula (I) of claim 1 and/or agrochemically acceptable salt thereofand/or agrochemically acceptable quaternized nitrogen derivative thereof

comprising reacting a compound of formula (II)

wherein W¹ represents an exchangeable radical or a leaving group with anamine of formula (III) or with an acid addition salt of the amine offormula (III)


19. The process as claimed in claim 18, wherein the exchangeable radicalor the leaving group Z¹ is selected from the group consisting offluorine, chlorine, bromine, iodine, (C₁-C₄)-alkylsulfanyl,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, unsubstituted orsubstituted phenyl-(C₁-C₄)-alkylsulfonyl and unsubstituted orsubstituted (C₁-C₄)-alkylphenylsulfonyl.
 20. The process as claimed inclaim 18, where a compound of formula (II-a)

in which Z¹ to Z³ are selected from the group consisting of COOH,COO(C₁-C₆)-alkyl, nitrile, C₂-C₆-alkynyl, halogen, acetyl, carbonyl and(C₁-C₆)-alkylmercapto; and W¹ represents an exchangeable radical or aleaving group selected from the group consisting of fluorine, chlorine,bromine, iodine, (C₁-C₄)-alkylsulfanyl, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-alkylsulfonyl, unsubstituted or substitutedphenyl-(C₁-C₄)-alkylsulfonyl and unsubstituted or substituted(C₁-C₄)-alkylphenylsulfonyl, is reacted with an amine or an acidaddition salt of formula (III)

giving initially an intermediate of formula (I-a)

and the intermediate of formula (I-a) obtained is then converted by aknown process into the compound (I).
 21. A process for preparing acompound of formula (I) of claim 1 and/or agrochemically acceptablesalts thereof and/or agrochemically acceptable quaternized nitrogenderivatives thereof

comprising condensing a compound of formula (IV) or an acid additionsalt thereof

with a compound of formula (V)

in which the radical Z⁴ represents (C₁-C₆)-alkoxy ordi-(C₁-C₆)-alkylamino.
 22. The process as claimed in claim 21, where thecompound of formula (IV) or the acid addition salt thereof

is condensed with a compound of formula (VI)

and a compound of formula (VII)

in which Z⁵ represents (C₁-C₆)-alkoxy or di-(C₁-C₆)-alkylamino and Z⁶represents (C₁-C₆)-alkoxy.
 23. A herbicidal composition or plantgrowth-regulating composition, comprising one or more compounds offormula (I) or salts thereof as claimed in claim
 1. 24. A method ofcontrolling one or more harmful plants or regulating growth of plants,comprising applying an effective amount of one or more compounds offormula (I) or salts thereof as claimed in claim 1 to plants, plantparts, plant seeds or an area under cultivation.
 25. A productcomprising one or more compounds of formula (I) or salts thereof asclaimed in claim 1 as one or more herbicides or plant growth regulators.